Carbohydrate based potential chemotherapeutic agents: Recent developments and their scope in future drug discovery

Mini-Reviews in Medicinal Chemistry

Volumn 12, Issue 14, 2012, Pages 1497-1519

  Tiwari, Vinod K ^a   Mishra, Ram C ^b   Sharma, Anindra ^c   Tripathi, Rama P ^c  

^a BANARAS HINDU UNIVERSITY   (India)

^b UNIVERSITY OF GEORGIA   (United States)

^c CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Antibiotics; Antitubercular agent; Carbohydrates; Drug development; Glycoconjugates; Glycopeptides; NIDDM

Indexed keywords

ALPHA GLUCOSIDASE INHIBITOR; ANTIBIOTIC AGENT; ANTIINFECTIVE AGENT; ANTIPARASITIC AGENT; ASCORBIC ACID; AZITHROMYCIN; CARBOHYDRATE DERIVATIVE; CARDIAC GLYCOSIDE; CETHROMYCIN; CLARITHROMYCIN; ERYTHROMYCIN; FIDAXOMICIN; GLUCOSE; GLUCOSE 6 PHOSPHATASE; GLYCOGEN PHOSPHORYLASE; GLYCOSIDASE INHIBITOR; HEPARIN; HYDROXAMIC ACID DERIVATIVE; ISOXAZOLINE DERIVATIVE; LINCOMYCIN; MITEMCINAL; MOENOMYCIN A; RIBOSE; ROXITHROMYCIN; TELAVANCIN; TELITHROMYCIN; TUBERCULOSTATIC AGENT; TUNICAMYCIN; UNINDEXED DRUG;

BIOLOGICAL ACTIVITY; CARBOHYDRATE ANALYSIS; COMBINATORIAL CHEMISTRY; CONJUGATE; DRUG CLASSIFICATION; DRUG RESEARCH; DRUG STRUCTURE; HUMAN; MALARIA; MENINGITIS; NEOPLASM; NONHUMAN; PHASE 1 CLINICAL TRIAL (TOPIC); PHASE 2 CLINICAL TRIAL (TOPIC); PHASE 3 CLINICAL TRIAL (TOPIC); RESPIRATORY TRACT INFECTION; REVIEW;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; BACTERIAL INFECTIONS; CARBOHYDRATES; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DISCOVERY; ENZYME INHIBITORS; GLUCOSIDASES; GLYCOCONJUGATES; GLYCOPEPTIDES; HUMANS; MODELS, MOLECULAR; MYCOSES; NEOPLASMS; PARASITIC DISEASES; VIRUS DISEASES;

EID: 84867349159     PISSN: 13895575     EISSN: 18755607     Source Type: Journal    
DOI: 10.2174/138955712803832654     Document Type: Review

References (140)

1. Whistler, R. L. and Smart, C. L. Polysaccharide chemistry. Academic Press: New York, 1953, pp 1-493.
2. Varki, A. Biological roles of oligosaccharides: all of the theories are correct. Glycobiology, 1993, 3, 97-130.
3. Lis, H.; Sharon, N. Lectins: Carbohydrate-specific proteins that mediate cellular recognition. Chem. Rev., 1998, 98, 637-674.
4. Rudd, P. M.; Elliott, T.; Cresswell, P.; Wilson, I. A.; Dwek, R. A. Glycosylation and the immune system. Science, 2001, 291, 2370-2376.
5. Bertozzi, C. R. and Kiessling, L. L. Chemical glycobiology. Science, 2001, 291, 2357-2364.
6. Dwek, R. A. Glycobiology: toward understanding the function of sugars. Chem. Rev., 1996, 96, 683-720.
7. Varki, A.; Freeze, H. H.; Vacquier, V. D. Glycans in development and systemic physiology. In Essentials of Glycobiology, 2nd ed. Varki, A.; Cummings, R. D.; Esko, J. D.; Freeze, H. H.; Stanley, P.; Bertozzi, C. R.; Hart, G. W.; Etzler, M. E., Eds. Cold Spring Harbor Laboratory Press: (NY), 2009, chapter 38.
8. Nogueira, C. M.; Parmanhan, B. R.; Farias P. P.; Corrêa, A. G. A importância crescente dos carboidratos em química medicinal. Rev. Virtual Quim., 2009, 1, 149-159.
9. Cao, H.; Hwang, J.; Chen. Xi. Carbohydrate-containing natural products in medicinal chemistry. InL Ed. Tiwari, V. K. & Mishra B.B. Opportunity, Challenge and Scope of Natural Products in Medicnal Chemistry, 2011: pp. 411-431.
10. Cipolla, L.; La Ferla, B.; Airoldi, C.; Zona, C.; Orsato, A.; Shaikh, N.; Russo, L.; Nicotra, F. Carbohydrate mimetics and scaffolds: sweet spots in medicinal chemistry. Fut. Med. Chem., 2010, 2, 587-599.
11. Cipolla, L.; Gregori, M.; So, P-W. Glycans in magnetic resonance imaging: determinants of relaxivity to smart agents, and potential applications in biomedicine. Curr. Med. Chem., 2011, 8, 1002-1018.
12. Cipolla, L.; Peri, F., Carbohydrate-based bioactive compounds for medicinal chemistry applications. Mini-Rev. Med. Chem., 2011, 11, 39-54.
13. Lonngren, J. Carbohydrates and the pharmaceutical industry. Pure Appl. Chem., 1989, 61, 1313-1314.
14. Horne, G.; Wilson, F. X. Therapeutic applications of iminosugars: current perspectives and future opportunities. Prog. Med. Chem., 2011, 50, 135-176.
15. Etayo, P.; Badorrey, R.; Villegas, M. D.; Galvez, G. A.; Víu, P. L. An expeditious method for the first asymmetric synthesis of Dexoxadrol from the chiral pool. Synlett., 2010, 1775-1778.
16. Okajima, T.; Irvine, K. D. Regulation of notch signaling by Olinked fucose. Cell, 2002, 111, 893-904.
17. Feizi, T. Oligosaccharides that mediate mammalian cell-cell adhesion. Curr. Opin. Struct. Biol., 1993, 3, 701-710.
18. Fukuda, M. Carbohydrate-dependent cell adhesion. Biorg. Med. Chem., 1995, 3, 207-215.
19. Lowe, J. B. Glycosylation, immunity, and autoimmunity. Cell, 2001, 104, 809-812.
20. Tripathi, R. P.; Singh, B.; Bisht, S. S.; Pandey, J., L-Ascorbic Acid in Organic Synthesis: An Overview. Curr. Org. Chem., 2009, 13, 99-122.
21. Angata, T.; Varki, A. Chemical diversity in the sialic acids and related alpha-keto acids: an evolutionary perspective. Chem. Rev., 2002, 102, 439-469.
22. Yu, H.; Cheng, J.; Ding, L.; Khedri, Z.; Chen, Y.; Chin, S.; Lau, K.; Tiwari, V. K.; Chen, X. Chemoenzymatic synthesis of GD3 oligosaccharides and other disialyl glycans containing natural and non-natural sialic acids. J. Am. Chem. Soc., 2009, 131, 18467-18477.
23. Inoue, S., Tsuruoka, T., Niida, T. The structure of nojirimycin, a piperidinose sugar antibiotic. J. Antibiot., 1966, 19, 288-292.
24. Asano, N. Sugar-mimicking glycosidase inhibitors: bioactivity and application. Cell. Mol. Life Sci., 2009, 66, 1479-1492.
25. Roedern, E. G. V.; Lohrf, E.; Hesseler, G.; Hoffmann, M.; Kesseler, H. Synthesis and Conformational Analysis of Linear and Cyclic Peptides Containing Sugar Amino Acids. J. Am. Chem. Soc., 1996, 118, 10156-10167.
26. Mishra, B. B.; Tiwari. V. K. Natural products: An evolving role in future drug discovery. Eur. J. Med. Chem., 2011, 46, 4769-4807.
27. Singh, G. S.; Panday, S. N. Natural products in discovery of potential and safer antibacterial agents. In Opportunity, Challenge & Scope of Natural Products in Med. Chem., Tiwari, V. K. & Mishra B. B. Eds. 2011; pp 63-102.
28. Ritter, T. K.; Wong, C. H. Carbohydrate-Based Antibiotics: A New Approach to Tackling the Problem of Resistance. Angew. Chem. Int. Ed. Engl., 2001, 40, 3508-3533.
29. Brandish, P. E.; Kimura, K. I.; Inukai, M.; Southgate, R.; Lonsdale, J. T.; Bugg, T. D. Modes of action of tunicamycin, liposidomycin B, and mureidomycin A: inhibition of phospho-N-acetylmuramylpentapeptide translocase from Escherichia coli. Antimicrob. Agents Chemother., 1996, 40, 1640-1644.
30. Somner, E. A.; Reynolds, P. E. Inhibition of peptidoglycan biosynthesis by ramoplanin. Antimicrob. Agents Chemother., 1990, 34, 413-419.
31. Blondeau, J. M. The evolution and role of macrolides in infectious diseases. Exp. Opin. Pharma., 2002, 3, 1131-1151.
32. Katz, L.; Ashley, G. W. Translation and protein synthesis: Macrolides. Chem. Rev., 2005, 105, 499-528.
33. Hammerschlag, M. R.; Sharma, R. Use of cethromycin, a new ketolide for treatment of community-acquired respiratory infections. Expert Opin. Inv. Drugs., 2008, 17, 387-400.
34. Stucki, A.; Gerber, P.; Acosta, F.; Cottagnoud, M.; Cottagnoud, P.; Jiang, L.; Nguyen, P.; Wachtel, D.; Wang, G.; Phan, L. T. Effects of EDP-420 on penicillin-resistant and quinolone-and penicillinresistant pneumococci in the rabbit meningitis model. J. Antimicrob. Chemother., 2008, 61, 665-669.
35. Dreier, J.; Amantea, E.; Kellenberger, L.; Page, M. G. P. Activity of the Novel Macrolide BAL19403 against Ribosomes from Erythromycin-Resistant Propionibacterium acnes. Antimicrob. Agents Chemother., 2007, 51, 4361-4365.
36. Onoma, M.; Yogo, K.; Ozaki, K.; Kamei, K.; Akima, M.; Koga, H.; Itoh, Z.; Omura, S.; Takanashi, H. Mitemcinal (GM-611), an orally active motilin receptor agonist, improves delayed gastric emptying in a canine model of diabetic gastroparesis. Clin. Exp. Pharmacol. Physiol., 2008, 35, 788-796.
37. Mason, D. J.; Dietz, A.; Deboer, C. Lincomycin, a new antibiotic: I. Discovery and biological properties. Antimicrob. Agents Chemother., 1962, 554-559.
38. Revill, P.; Serradell, N.; Bolos, J. Tiacumicin B. Macrolide antibiotic, Treatment of C. difficile-associated diarrhea. Drugs Fut., 2006, 31, 494-497.
39. Savage, G. M. Lincomycin and clindamycin: Their role in chemotherapy of anaerobic and microaerophilic infections. Infection, 1974, 2, 152-159.
40. Hansen, L. H.; Mauvais, P.; Douthwaite, S. The macrolide-ketolide antibiotic binding site is formed by structures in domains II and V of 23S ribosomal RNA. Mol. Microbiol., 1999, 31, 623-631.
41. Taylor, J. G.; Li, X.; Oberthur, M.; Zhu, W.; Kahne, D. E. The Total Synthesis of Moenomycin A. J. Am. Chem. Soc., 2006, 128, 15084-15085.
42. Williams, D. H. and Bardsley, B. The Vancomycin group of Antibiotics and the fight against resistant bacteria. Angew. Chem. Int. Ed. Engl., 1999, 38, 1172-1193.
43. Billeter, M.; Zervos, M. J.; Chen, A. Y.; Dalovisio, J. R.; Kurukularatne, C. Dalbavancin: a novel once-weekly lipoglycopeptide antibiotic. Clin. Infect. Dis., 2008, 46, 577-583.
44. Farver, D. K.; Hedge, D. D.; Lee, S. C. Ramoplanin: A Lipoglycodepsipeptide Antibiotic. Ann. Pharmacother., 2005, 39, 863-868.
45. Fulco, P.; Wenzel, R. P. Ramoplanin: a topical lipoglycodepsipeptide antibacterial agent. Expert Rev. Anti-Infect. Ther., 2006, 4, 939-945.
46. D'Alonzo, D.; Guaragna, A.; Palumbo, G. Glycomimetics at the mirror: medicinal chemistry of L-iminosugars. Curr. Med. Chem., 2009, 16, 473-505.
47. Asano, N. Glycosidase inhibitors: update and perspectives on practical use. Glycobiology, 2003, 13, 93-104.
48. Truscheit, E.; Frommer, W.; Junge, B.; Müller, L.; Schmidt, D. D.; Wingender, W. Chemistry and Biochemistry of Microbial β-Glucosidase Inhibitors. Angew. Chem. Int. Edn. Engl., 1981, 20, 744-761.
49. Neufeld, E. F., Lysosomal storage diseases. Ann. Rev. Biochem., 1991, 60, 257-280.
50. Tifft, C. J.; Proja, R. L. Stemming the tide: glycosphingolipid synthesis inhibitors as therapy for storage diseases. Glycobiology, 2000, 10, 1249-1258.
51. Platt, F. M.; Neises, G. R.; Dwek, R. A.; Butters, T. D. Nbutyldeoxynojirimycin is a novel inhibitor of glycolipid biosynthesis. J. Biol. Chem., 1994, 269, 8362-8365.
52. von Itzstein, M.; Wu, W. Y.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Van Phan, T.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Coleman, P. M.; verghese, J. N.; Ryan, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M.; and Penn, C. R., Rational design of potent sialidase-based inhibitors of influenza virus replication. Nature, 1993, 363, 418-423.
53. Li, J.; Zheng, M.; Tang, W.; He, P. L.; Zhu, W.; Li, T.; Zuo, J. P.; Liu, H.; Jiang, H., Syntheses of triazole-modified zanamivir analogues via click chemistry and anti-AIV activities. Bioorg. Med. Chem. Lett., 2006, 16, 5009-5013.
54. Tewari, N.; Tiwari, V. K.; Mishra, R. C.; Tripathi, R. P.; Srivastava, A. K.; Ahmad, R.; Srivastava, R.; Srivastava, B. S. Synthesis and bioevaluation of glycosyl ureas as β-glucosidase inhibitors and their effect on mycobacterium. Bioorg. Med. Chem., 2003, 11, 2911-2922.
55. Khan, A. R.; Tiwari, V. K.; Ahmad, R.; Srivastava, A. K.; Tripathi, R. P., Synthesis of alpha-mannosylated phenolics as β-glucosidase inhibitors. J. Enz. Inhib. Med. Chem., 2004, 19, 107-112.
56. Anand, N.; Jaiswal, N.; Pandey, S. K.; Srivastava, A. K.; Tripathi, R. P. Application of click chemistry towards an efficient synthesis of 1,2,3-1H-triazolyl glycohybrids as enzyme inhibitors. Carbohyd. Res. 2011, 346, 16-25.
57. Singh, N.; Pandey, S. K.; Tripathi, R. P.; Regioselective [3+2]cycloaddition of chalcones with a sugar azide: easy access to 1-(5-deoxy-D-xylofuranos-5-yl)-4,5-disubstituted-1H-1,2,3-triazoles: Carbohyd. Res., 2010, 243, 1641-1648.
58. Rossi, L. L.; Basu, A. Glycosidase inhibition by 1-glycosyl-4-phenyl triazoles. Bioorg. Med. Chem. Lett., 2005, 15, 3596-3599.
59. Ferrari, P.; Ferrandi, M.; Valentini, G.; Manunta, P.; Bianchi, G. Targeting Ouabain-and Adducin-dependent mechanisms of hypertension and cardiovascular remodeling as a novel pharmacological approach. Med. Hypotheses, 2007, 68, 1307-1314.
60. Hollman, A. Drugs for atrial fibrillation. Digoxin comes from Digitalis lanata. British Med. J. 1996, 312, 912.
61. Master, J.; Schweitzer, P. Is there a role for digoxin in atrial fibrillation without heart failure? Cardiol. J. 2009, 16, 483-486.
62. The Digitalis Investigation Group. The effect of digoxin on mortality and morbidity in patients with heart failure. New Eng. J. Med., 1997, 336, 525-533.
63. Maryanoff, B. E.; Costanzo, M. J.; Nortey, S. O.; Greco, M. N.; Shank, R. P.; Schupsky, J. J.; Ortegon, M. P.; Vaught, J. L., Structure-activity studies on anticonvulsant sugar sulfamates related to topiramate. Enhanced potency with cyclic sulfate derivatives. J. Med. Chem., 1998, 41, 1315-1343.
64. Jeon, K.; Byun, M.; Jue, D. Gold compound auranofin inhibits IkappaB kinase (IKK) by modifying Cys-179 of IKK beta subunit. Exp. Mol. Med., 2003, 35, 61-66.
65. Wang, Z.; Gleichmann, H. GLUT2 in pancreatic islets: crucial target molecule in diabetes induced with multiple low doses of streptozotocin in mice. Diabetes, 1998, 47, 50-56.
66. Brentjens, R.; Saltz, L. Islet cell tumors of the pancreas: the medical oncologist's perspective. Surg. Clinics North Am., 2001, 81, 527-542.
67. Clausen, M. R.; Mortensen, P. B. Lactulose, disaccharides and colonic flora. Clinical consequences. Drugs, 1997, 53, 930-942.
68. DiJoseph, J.F.; Dougher, M.M.; Armellino, D.C.; Evans, D.Y.; Damle, N.K. Therapeutic potential of CD22-specific antibodytargeted chemotherapy using inotuzumab ozogamicin (CMC-544) for the treatment of acute lymphoblastic leukemia. Leukemia, 2007, 21, 2240-2245.
69. Erickson, H. K.; Park, P. U.; Widdison, W. C.; Kovtun, Y. V.; Garrett, L. M.; Hoffman, K.; Lutz, R. J.; Goldmacher, V. S.; Blattler, W. A. Antibody-maytansinoid conjugates are activated in targeted cancer cells by lysosomal degradation & linker-dependent intracellular processing. Cancer Res., 2006, 66, 4426-4433.
70. Robbins, J. B. S., R.; Szu, S. C.; Pozsgay, V. Bacterial polysaccharide-protein conjugate vaccines. Pure Appl. Chem., 1999, 71, 745-754.
71. Verez-Bencomo, V.; Fernandez-Santana, V.; Hardy, E.; Toledo, M. E.; Rodriguez, M. C.; Heynngnezz, L.; Rodriguez, A.; Baly, A.; Herrera, L.; Izquierdo, M.; Villar, A.; Valdes, Y.; Cosme, K.; Deler, M. L.; Montane, M.; Garcia, E.; Ramos, A.; Aguilar, A.; Medina, E.; Torano, G.; Sosa, I.; Hernandez, I.; Martinez, R.; Muzachio, A.; Carmenates, A.; Costa, L.; Cardoso, F.; Campa, C.; Diaz, M.; Roy, R. A synthetic conjugate polysaccharide vaccine against Haemophilus influenzae type b. Science, 2004, 305, 522-525.
72. Clark, I. A.; Schofield, L., Pathogenesis of malaria. Parasitol Today, 2000, 16, 451-454
73. Greenwood, B. M.; Fidock, D. A.; Kyle, D. E.; Kappe, S. H.; Alonso, P. L.; Collins, F. H. and Duffy, P. E., Malaria: progress, perils, and prospects for eradication, J. Clin. Invest., 2000, 118, 1266-1276.
74. Hewitt, M. C.; Snyder, D. A.; Seeberger, P. H. Rapid synthesis of a glycosylphosphatidylinositol-based malaria vaccine using automated solid-phase oligosaccharide synthesis. J. Am. Chem. Soc., 2002, 124, 13434-13436.
75. Fuster, M. M.; Esko, J. D. The sweet and sour of cancer: glycans as novel therapeutic targets. Nat. Rev. Cancer, 2005, 5, 526-542.
76. Kozbor, D. Cancer vaccine with mimotopes of tumor-associated carbohydrate antigens. Immunologic Res., 2010, 46, 23-31.
77. Borman, S. Improving vaccines aimed at cancer. Chem. Eng. News, 2011, 89, 53-57.
78. Tripathi, R. P.; Tewari, N.; Dwivedi, N.; Tiwari, V. K. Fighting tuberculosis: An old disease with new challenges. Med. Res. Rev. 2005, 25, 93-131.
79. Kishore, N.; Mishra, B. B.; Tripathi, V.; Tiwari, V. K. Alkaloids as potential Anti-tubercular agents. Fitoterapia, 2009, 80, 149-163.
80. Chaturvedi, V.; Dwivedi, N.; Tripathi, R. P.; Sinha, S. Evaluation of Mycobacterium smegmatis as a possible surrogate screen for selecting molecules active against multi-drug resistant Mycobacterium tuberculosis. J. Gen. Appl. Microb., 2007, 53, 333-337.
81. Trias, J.; Benz, R. Mycobacterial cell wall: Structure and role in natural resistance to antibiotics. Mol. Microbiol., 1994, 19, 283-295.
82. Rastogi, N. K.; Goh, S.; David, H. L. Antimicrob. Agents Chemother. 1990, 34, 750.
83. Russell, A. D. Mechanisms of Bacterial Resistance to Antibiotics and Biocides. Prog. Med. Chem., 1998, 35, 133-197.
84. Brennan, P. J.; Nikaido, H. The envelope of mycobacteria. Ann. Rev. Biochem., 1995, 64, 29-63.
85. Tripathi, R. P.; Tripathi, R.; Tiwari, V. K.; Bala, L.; Sinha, S.; Srivastava, A.; Srivastava, R.; Srivastava, B. S. Synthesis of glycosylated beta-amino acids as new class of antitubercular agents. Eur. J. Med. Chem., 2002, 37, 773-781.
86. Khan, A. R.; Tripathi, R. P.; Tiwari, V. K.; Mishra, R. C.; Reddy, V. J. M.; Saxena, J. K. Conjugate addition of amines to sugar derived olefinic esters: Synthesis of glycosylated amino esters as DNA topoisomerase-II inhibitors. J. Carbohyd. Chem., 2002, 21, 591-604.
87. Tiwari V. K.; Tripathi R. P.; Tripathi R.; Bala L.; Sinha S.; Srivastava R.; Srivastava B.S. Search of new drugs for tuberculosis: Glycosylated G-amino acids as new class of antitubercular agents. Trends Carbohyd. Chem., 2002, 8, 67-76.
88. Van-Heijennoort, J. Recent advances in the formation of glycan chains in the synthesis bacterial peptidoglycan. Glycobiology, 2001, 11. 25-26
89. Scherman, M,; Weston, A.; Duncan, K.; Whittington, A.; Upton, R.; Deng, L.; Comber, R.; Friedrich, J. D.; Neil, M. R. Biosynthetic origin of mycobacterial cell wall arabinosyl residues. J. Bacteriol., 1995, 177, 7125-7130.
90. Katiyar, D.; Tiwari, V. K.; Tewari, N.; Verma, S. S.; Sinha, S.; Gaikwad, A.; Srivastava, A. K.; Chaturvedi, V.; Srivastava, R.; Srivastava, B. S.; Tripathi, R. P. Synthesis and Antimycobacterial Activities of Glycosylated Amines and Amino Alcohols. Eur. J. Med. Chem., 2005, 40, 351-360.
91. Tripathi, R. P.; Tiwari, V. K.; Tewari, N.; Katiyar, D.; Saxena, N.; Sinha, S.; Gaikwad, A.; Srivastava, A. K.; Chaturvedi, V.; Manju, Y. K.; Srivastava, R.; Srivastava, B. S. Synthesis and antitubercular activities of bis-glycosylated diamino alcohols. Bioorg. Med. Chem., 2005, 13, 5668-5679.
92. Tewari, N.; Tiwari, V. K.; Tripathi, R. P.; Gaikwad, A.; Sinha, S.; Shukla, P. K.; Srivastava, R.; Srivastava, B. S. Synthesis of Galactopyranosyl Amino Alcohols as a new class of antitubercular and antifungal agents. Bioorg. Med. Chem. Lett., 2004, 12, 329-332.
93. Tiwari, V. K.; Tripathi, R. P. Unexpected Isomerisation of Double bond with DBU: A Convenient Synthesis of Tetrasubstituted alphaalkylidene tetrahydrofuranoses. Ind. J. Chem., 2002, 41B, 1681-1685.
94. Pandey, J.; Tiwari, V. K.; Verma, S. S.; Chaturvedi, V.; Sinha, S.; Tripathi, R. P. Synthesis and antitubercular screening of imidazole derivatives. Eur. J. Med. Chem., 2009, 44, 3350-3355.
95. Tiwari, V. K.; Singh, B. K.; Chaturvedi, V.; Manju, Y. K.; Srivatava, A. K.; Sinha, S.; Gaikwad, A.; Tripathi, R. P. Synthesis and Antitubercular Activities of S-Glycosyl Mercaptans. Org. Chem. Ind. J. 2007, 3, 84-96.
96. Novel phenyl cyclopropyl methanones useful as antitubercular agents. Grover, R. K.; Mishra, R. C.; Verma, S. S.;Tripathi, R. P.; Roy, R.; Srivastava, R.; Srivastava, A. Chaturvedi, V.; Krishana, M.Y.; Srivasatava, B. S.; Lal, J.; Gupta, R. C 036DEL2004 Filing Date 31/3/04 New Delhi.
97. Lal, J.; Tripathi, R. P.; Gupta, R. C. Pharmacokinetics and excretion of the novel anti-tuberculosis compound 1,2:5,6-di-Oisopropylidene-3-O-(phenyl cyclopropyl methanonyl)-alpha-Dglucofuranose (S-001-14) after oral doses in rats. Arzneimittel-Forsch, 2008, 58, 410-418.
98. Dwivedi, N.; Tewari, N.; Tiwari, V. K.; Chaturvedi, V.; Manju, Y. K.; Srivastava, A.; Giakwad, A.; Sinha, S.; Tripathi, R. P. An efficient synthesis of aryloxyphenyl cyclopropyl methanones: a new class of anti-mycobacterial agents. Bioorg. Med. Chem. Lett., 2005, 15, 4526-4530.
99. Srivastava, S. K.; Tripathi, R. P.; Ramachandran, R., NAD(+)-dependent DNA ligase (Rv3014c) from M. tuberculosis H37Rv: crystal structure of the adenylation domain and identification of novel inhibitors. J. Biol. Chem., 2005, 280, 30273-30281.
100. Srivastava, S. K.; Dube, D.; Tewari, N.; Dwivedi, N.; Tripathi, R. P.; Ramchandran, R. Mycobacterium tuberculosis NAD+-dependent DNA ligase is selectively inhibited by glycosylamines compared with human ligase I. Nucleic Acid Res., 2005, 33, 7090.
101. Dube, D.; Kukshal, V.; Srivastava, S. K.; Tripathi, R. P.; Ramachandran, R. NAD(+)-dependent DNA ligase (Rv3014c) from M-tuberculosis: Strategies for inhibitor design. Med. Chem. Res., 2008, 17, 189-198.
102. Dwivedi, N.; Dube, D.; Pandey, J.; Singh, B. K.; Ramchandran, R.; Tripathi, R. P. NAD(+)-dependent DNA ligase: A novel target waiting for the right inhibitor. Med. Res. Rev., 2008, 28, 545-568.
103. Tripathi, R. P.; Pandey, J.; Kukshal, V.; Arya A.; Mishra, M.; Dube, D.; Chopra, D.; Dwivedi, R.; Chaturvedi, V.; Ramachandran, R. Synthesis of dispiro-cycloalkanones, their in silico screening and bioevaluation as antituberculosis and mycobacterial NAD+-dependent DNA ligase inhibitors. Med. Chem. Commun., 2011, 2, 378-384.
104. Tripathi, R. P.; Katiyar, D.; Dwivedi, N.; Singh, B. K.; Pandey, J. Recent developments in search of antifilarial agents. Curr. Med. Chem., 2006, 13, 3319-3334.
105. Tiwari, V. K.; Tewari, N.; Katiyar, D.; Tripathi, R. P.; Arora, K.; Gupta, S.; Ahmad, R.; Srivastava, A. K.; Khan, M. A.; Murthy, P. K.; Walter, R. D., Synthesis and antifilarial evaluation of N-1, Nn-xylofuranosylated diaminoalkane. Bioorg. Med. Chem., 2003, 11, 1789-1800.
106. Srivastava, A. K.; Tripathi, R. P.; Khan, A. R.; Bhaduri, A. P.; Singh, S. N.; Chatterjee, R. K. Effect of 3-O-(aminoalkyl)-Dgluco (xylo) furanoses on glutathione metabolism of falarial parasites. Helminthologia, 1995, 32, 25-27
107. Khan, A. R.; Tripathi, R. P.; Bhaduri, A. P.; Sahai, R.; Puri, A.; Tripathi, L. M.; Srivastava, V. M. L. Synthesis and immunomodulatory activities of 2'-hydroxy-3'-N, N-Disubstituted aminopropyl-β-D-glucofuranoses as immunomodulators. Eur. J. Med. Chem., 2001, 36, 103-106.
108. Arora, K.; Mishra, R. C.; Tripathi, R. P.; Srivastava, A. K.; Walter, R. D. Glutathione synthesis in felarial worms: An attractive target for the design and synthesis of new antifilaruls. Med. Chem. Res., 2004, 13, 687-706.
109. Gupta, S.; Arora, K.; Tiwari, V. K.; Katiyar, D.; Tripathi, R. P.; Srivastava, A. K.; Walter, R. D. Inhibitors of filarial gammaglutamyl cycle enzymes as possible macrofilaricidal agents. Med. Chem. Res., 2004, 13, 707-723.
110. Mishra, R. C.; Dwivedi, N.; Tripathi, R. P.; Bansal, I.; Saxena, J. K. Synthesis and DNA topoisomerase-II inhibitory activity of unnatural nucleosides. Nucleos. Nucleot. Nucl., 2005, 24, 15-35.
111. Kaur, J.; Singh, N.; Singh, B. K.; Dube, A.; Tripathi, R. P.; Singh, P; Singh, N. Leishmania donovani: Oral therapy with glycosyl 1,4-dihydropyridine analogue showing apoptosis like phenotypes targeting pteridine reductase 1 in intracellular amastigotes. Exp. Parasit., 2010, 125, 310-314.
112. Pandey, V. P.; Bisht, S. S.; Mishra, M.; Kumar, A.; Siddiqi, M. I.; Verma, A.; Mittal, M.; Sane, S. A.; Gupta, S.; Tripathi, R. P. Synthesis and molecular docking studies of 1-phenyl-4-glycosyldihydropyridines as potent antileishmanial agents. Eur. J. Med. Chem., 2010, 45, 2381-2388.
113. Mishra, B. B.; Singh, R. K.; Srivastava, A.; Tripathi, V. J.; Tiwari, V. K. Fighting Against Leishmaniasis: Search of Alkaloids as Future True Potential Anti-Leishmanial Agents. Mini-Rev. Med. Chem., 2009, 9, 107-123.
114. Tewari, N.; Ramesh, Mishra, R. C.; Gupta, S.; Tripathi, R. P. Phenylene bridged bis-glycosyl ureides as potential antileishmanial agents. Bioorg. Med. Chem. Lett., 2004, 14, 4055-4059.
115. Tripathi, R. P.; Mishra, R. C.; Dwivedi, N.; Tewari, N.; Verma, S. S. Current status of malaria control. Curr. Med. Chem., 2005, 12, 2643-2659.
116. Mishra, R. C.; Tripathi, R.; Katiyar, D.; Tewari, N.; Singh, D.; Tripathi, R. P. Synthesis of glycosylated beta-amino hydroxamates as new class of antimalarials. Bioorg. Med. Chem., 2003, 11, 5363-5374.
117. Mishra, R. C.; Tewari, N.; Verma, S. S.; Tripathi, R. P.; Kumar, M.; Shukla, P. K. Diastereoselective synthesis and antifungal activity of glycosyl isoxazolines. J. Carbohyd. Chem., 2004, 23, 353-374.
118. Tripathi, R. P.; Singh, V.; Khan, A. R.; Bhaduri, A. P.; Savena, G.; Chandra, K. Synthesis and antiviral activities of 3-O-(aminoalkyl)-1,2-O-isopropylidine-D-gluco(xylo) foranoses. Ind. J. Chem., 1995, 34B, 791-795.
119. Poletti, L.; Lay, L. Chemical Contributions to Understanding Heparin Activity: Synthesis of Related Sulfated Oligosaccharides. Eur. J. Org. Chem., 2003, 2999-3024
120. Capila, I.; Linhardt, R. J. Heparin-protein interactions. Angew. Chem. Int. Ed. Engl., 2002, 41, 391-412.
121. Lane, D. A.; Ryan, K. Heparin and low molecular weight heparin: is anti-factor Xa activity important? J. Lab. Clin. Med., 1989, 114, 331-333.
122. El Hadri, A.; Petitou, M. Rational Design of Anticoagulant Drugs Using Oligosaccharide Chemistry. Chimia Int. J. Chem., 2011, 65, 14-17.
123. Dwivedi, N.; Bisht, S. S.; Tripathi, R. P. Asymmetric organocatalysis with glycosyl-beta-amino acids: direct asymmetric aldol reaction of acetone with aldehydes. Carbohyd. Res., 2006, 341, 2737-2743.
124. Singh, N.; Pandey, J.; Tripathi, R. P. DGlucosamine, a natural aminosugar as organocatalyst for an ecofriendly direct aldol reaction of ketones with aromatic aldehydes in water. Catal. Commun., 2008, 9, 743-746.
125. Pandey, J.; Dwivedi, N.; Singh, N.; Srivastava, A. K.; Tamarkar, A.; Tripathi, R. P. Diastereoselective synthesis of glycosylated prolines as alpha-glucosidase inhibitors and organocatalyst in asymmetric aldol reaction. Bioorg. Med. Chem. Lett., 2007, 17, 1321-1325.
126. Mishra, R. C.; Tewari, N.; Arora, K.; Ahmad, R.; Tripathi, R. P.; Tiwari, V. K.; Walter, R. D.; Srivastava, A. K. DBU-assisted cyclorelease elimination: Combinatorial synthesis and gammaglutamyl cysteine synthetase and glutathione-S-transeferase modulatory effect of C-nucleoside analogs. Comb. Chem. Highthro. Scr., 2003, 6, 37-50.
127. Tewari, N.; Mishra, R. C.; Tiwari, V. K.; Tripathi, R. P. DBU catalyzed cyclative amidation reaction: A convenient synthesis of C-nucleoside analogs. Synlett., 2002, 1779-1782.
128. Mishra, R. C.; Katiyar, D.; Tewari, N.; Tripathi, R. P. A versatile synthesis of Dihydropyrimidinone C-nucleosides. Nucleosides, Nucleotides Nucleic Acid, 2004, 23, 531-544.
129. Katiyar, D.; Mishra, R. C.; Tripathi, R. P. Diastereoselective Synthesis of Galactopyranosyl Amino Esters and their Transformations into C-nucleosides. J. Carbohyd. Chem., 2004, 23, 49-70.
130. Tewari, N.; Katiyar, D.; Tiwari, V. K.; Tripathi, R. P. Amberlite IR-120 catalysed efficient synthesis of glycosyl enamines and their application. Tetrahedron Lett., 2003, 44, 6639-6642.
131. Tiwari V. K.; Tewari, N.; Katiyar, D.; Tripathi, R. P. One-pot Amberlite IR-120 catalysed synthesis of glycosyl dihydropyridones. Monatsh. Chem., 2007, 138, 1297-1302.
132. Verma, S. S.; Dwivedi, N.; Singh, B. K.; Tripathi, R. P. DBU assisted expeditious synthesis of glycosyl dienes via glycosylated beta-hydroxy esters. Carbohyd. Res., 2006, 341, 1930-1937.
133. Tewari, N.; Dwivedi, N.; Tripathi, R. P. Tetrabutylammonium Hydrogen Sulphate Catalysed Eco-friendly and Efficient Synthesis of Glycosyl 1,4-Dihydropyridines. Tetrahedron Lett., 2004, 45, 9011-9014.
134. Dwivedi, N.; Mishra, R. C.; Tripathi, R. P. Tetrabutylammonium Hydrogensulphate Catalysed Efficient Synthesis of Glycosyl(aryl) Dihydropyrimidinones. Lett. Org. Chem., 2005, 2, 450-457.
135. Singh, B. K.; Verma, S. S.; Dwivedi, N.; Tripathi, R. P. L-ascorbic acid in organic synthesis: DBU-catalysed one-pot synthesis of tetramic acid derivatives from 5,6-O-isopropylidene ascorbic acid. Tetrahedron Lett., 2006, 47, 2219-2222.
136. Bisht, S. S.; Dwivedi, N.; Tripathi, R. P. L-Ascorbic acid in organic synthesis: a facile synthesis of 4-(butenolide-5-methylidenyl)-1,4-dihydropyridines. Tetrahedron Lett., 2007, 48, 1187-1189.
137. Tripathi, R. P.; Dwivedi, N.; Singh, N.; Mishra, M. Synthesis and antitubercular activity of nucleoside analogs based on L-ascorbic acid and bases. Med. Chem. Res., 2008, 17, 53-61
138. Tripathi, R. P.; Rastogi, S. K.; Kundu, B.; Saxena, J. K.; Reddy, V. J. M.; Srivastava, S.; Chandra, S.; Bhaduri, A.P. Identification of inhibitors of DNA Topoisomerase-II from a synthetic library of glycoconjugates. Combi. Chem. Highthro. Scr., 2001, 4, 237-244.
139. Tripathi, R. P.; Shukla, P. K.; Sinha, S.; Srivastava, R.; Srivastava, K. K.; Chaturvedi, V.; Srivastava, A.; Srivastava, B. S. A novel combinatorial library of 3-substituted amino-3-glycosylated propanamides useful as antifungal and antibacterial agents. 1529DEL2004, Patent No.: 196956, 23/06/2006.
140. Pandey, J.; Sharma, A.; Tiwari, V. K.; Dube, D.; Ramachandran, R.; Chaturvedi, V.; Sinha, S. K.; Mishra, N. K.; Shukla, P. K.; Tripathi, R. P. Solution phase synthesis of a library of carbapeptide analogues based on glycosylamino acid scaffolds, their in silico screening and antimicrobial evaluation. J. Comb. Chem., 2009, 11, 422-427.