Recent trends in the chemistry of privileged scaffold: 1,4-benzodiazepine

International Journal of Pharma and Bio Sciences

Volumn 4, Issue 1, 2013, Pages 485-513

  Kaur, Navjeet ^a  

^a BANASTHALI UNIVERSITY   (India)

Author keywords

1,4 Benzodiazepines; Privileged scaffold; Reactions

Indexed keywords

1,4 BENZODIAZEPINE; 2,3 DIAMINOPROPIONIC ACID; 5 FORMYLIMIDAZOLE; ALANINE; AMINE; AMMONIA; ANTHRANILIC ACID DERIVATIVE; BENZODIAZEPINE DERIVATIVE; BENZOPHENONE; BETA ALANINE; CARBANION; CYANIDE; DIETHYLNITROSAMINE; DILACTAM; GRIGNARD REAGENT; HYDROGEN SULFIDE; IMIDAZOLE DERIVATIVE; INDOLE; ION; ISOCYANATE; LACTAM DERIVATIVE; LOTRAFIBAN; METHYLAMINE; MOLECULAR SCAFFOLD; NUCLEOPHILE; PALLADIUM; QUINOLINE; SODIUM CHLORIDE; TOSYLMETHYL ISOCYANIDE; UNCLASSIFIED DRUG; 1 METHYL 6 PHENYL 4H STRIAZOLO[4,3 A][1,4]BENZODIAZEPINE; 1,4 BENZODIAZEPINEDIONE DERIVATIVE; 11 CHLOROPYRROLO[2,1 C][1,4]BENZODIAZEPINE DERIVATIVE; 2 PHENYL 2,3,4,5 TETRAHYDRO 1H 1,4 BENZODIAZEPINE; 2,4 DIMETHYL 1,4 BENZODIAZEPINE DERIVATIVE; 2,4 DIPHENYL 1,4 BENZODIAZEPINE DERIVATIVE; 3 (HYDROXYALKYL) 1,4 BENZODIAZEPIN 2 ONE DERIVATIVE; 3 ACETOXY 1,4 BENZODIAZEPINE; 4 CHLORO 5 METHOXY 2 NITROPYRIDAZINE 3 ONE; 5 CHLORO 1,4 BENZODIAZEPIN 2,5 DIONE; 7 BROMO 3 (1 HYDROXY 1 PHENYLMETHYL) 1 METHYL 5 (2 PYRIDYL) 2,3 DIHYDRO 1H 1,4 BENZODIAZEPIN 2 ONE; 7 CHLORO 2 (DI 4 MORPHOLINYLPHOSPHINYLOXY) 5 PHENYL 3H 1,4 BENZODIAZEPINE; 7 CHOLORO 1,3 DIHYDRO 5 PHENYL 2H 1,4 BENZODIAZEPIN 2 ONE DERIVATIVE; BENZO 1,4 DIAZEPIN 3 ONE DERIVATIVE; BENZODIAZEPIN 2 ONE DERIVATIVE; BENZODIAZEPINE; CHEMICAL COMPOUND; DIETHYL (1 METHYL 2,3,4,5 TETRAHYDRO 1H 1,4 BENZODIAZEPIN 4 YLMETHYL)PHOSPHONATE; IMIDAZO[1,2 A][1,4]BENZODIAZEPINE DERIVATIVE; NORDAZEPAM; PYRROLO[2,1 C][1,4]BENZODIAZEPINE; QUINOLONE; QUIZOLINO[1,4]BENZODIAZEPINE;

1,6 ELIMINATION; ACETYLATION; ACYLATION; ADDITION REACTION; ALDOL REACTION; ALKYLATION; ALPHA ALKYLATION; AMINATION; AMINO ACID SYNTHESIS; AMINOCARBONYLATION; AMINOETHYLATION; AROMATIZATION; ARTICLE; AZIDATION; BENZOYLISATION; BENZYLATION; BOC PROTECTION; CARBAMOYLATION; CHEMICAL REACTION; CLOKE REARRANGEMENT; COUPLING REACTION; CROSS COUPLING REACTION; CYCLIZATION; CYCLOADDITION; DECOMPOSITION; DEGRADATION; DEPROTONATION; DIAZOTIZATION; EGUCHI AZA WITTIG REACTION; ELECTROPHILIC ADDITION; ELIMINATION REACTION; ENANTIOSELECTIVITY; EPIMERIZATION; EPOXIDATION; FLUORESCENCE; FLUORINATION; FREE RADICAL REACTION; HECK REACTION; HYDROLYSIS; INTERACTIONS WITH DNA; INVERSION TRAPPING; IODINATION; IOZINATION; LINKER FORMATION; MASS FRAGMENTATION; METABOLISM; METHOXYLATION; METHYLATION; NITRATION; ORGANIC CHEMISTRY; OXIDATION; PHOSPHORYLATION; PHOTODEGRADATION; POLONOVSKY REARRANGEMENT; PYROLYSIS; RACEMIZATION; REDUCTION; RING CONTRACTION; RING OPENING; SANDMEYER REACTION; SAPONIFICATION; STAUDINGER REACTION; STOICHIOMETRY; STRECKER SYNTHESIS; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; SUZUKI REACTION; SYNTHESIS; TREND STUDY; VILSMEIER HAACK REACTION; CARBONYLATION; CATALYSIS; CHEMICAL INTERACTION; DEGRADATION KINETICS; ELECTROPHILICITY; FLUORESCENCE ANALYSIS; NUCLEOPHILICITY; PROTON TRANSPORT; REACTION ANALYSIS; WITTIG REACTION;

EID: 84879819890     PISSN: None     EISSN: 09756299     Source Type: Journal    
DOI: None     Document Type: Article

References (65)

1. Paul Y, Tyagi S, Singh B, Formulation and evaluation of taste masked dispersible tablets of zidovudine, Int. J. Pharma and Bio. Sci., 2, 20 (2011).
2. Rao NGR, Ghurghure SM, Munde M, Hadi A, Design and characterization of gas powered system of zidovudine using synthetic polymers, Int. J. Pharma and Bio. Sci., 2, 269 (2011).
3. Avdagic A, Lesac A, Sunjic V, First examples of the solvent effect on absolute conformation of chiral 3,3- disubstituted 1,4-benzodiazepin-2-ones, Tetrahedron, 55, 1407 (1999).
4. Cepanec I, Litvic M, Pogorelic I, Efficient Synthesis of 3-Hydroxy-1,4- benzodiazepines Oxazepam and Lorazepam by New Acetoxylation Reaction of 3-Position of 1,4- Benzodiazepine Ring, Org. Process Res. Dev. 10, 1192 (2006).
5. Naim HA, Zakariyya NI, Synthesis of NSubstituted Quinazolino[1,4]- benzodiazepine: A Facial Route to NBenzylsclerotigenin, Acta. Chim. Slov. 52, 328 (2005).
6. Offel M, Pornth PL, Singh H, Billington DC, Bunprakob Y, Sattayasai J, Lattmann E, Synthesis of substituted 3- anilino-5-phenyl-1,3-dihydro-2H-1,4- benzodiazepine-2-ones and their evaluation as cholecystokinin-ligands, Arch. Pharm. Chem. Life Sci. 339, 163 (2006).
7. Bartnett DW, Paginot MJ, Curley RW, Stereoselective route to 15N-labeled-β- deuterated amino acids: synthesis of (2S,3R)-[3-2H,15N]-phenylalanine, Tetrahedron: Asymmetry, 13, 1893 (2002).
8. Santos F, Javier G, Carlos P, 1,4- Benzodiazepine N-Nitrosoamidines: Useful Intermediates in the Synthesis of Tricyclic Benzodiazepines, Molecules 11, 583 (2006).
9. Dragan S, Zdenko H, Vitomir S, Aldol derivatives of 5-phenyl-1,4- benzodiazepin-2-on-N-oxide; intriguing inertness of N-oxides in aldol reactions, ARKIVOC (xiv), 8 (2003).
10. Ian PA, Richard JA, Neil FB, Richard KB, Gary FB, John SC, Stephen KE, Jerome FH, Nigel H, David OM, Andrew CS, Stephen ACS, Timothy CW, Andrew SW, A new synthesis of the GPIIb/IIIa receptor antagonist SB-214857-A, Tetrahedron Lett. 42, 4915 (2001).
11. Carlier PR, Zhao H, DeGuzman J, Lam PCH, Enantioselective synthesis of "quaternary" 1,4-benzodiazepin-2-one scaffolds via memory of chirality, J. Am. Chem. Soc. 125, 11482 (2003).
12. Ishikura M, Mori M, Terashima MBY, A new synthesis of anthramycin via palladium-catalyzed carbonylation, J. Chem. Soc. Chem. Commun. 741 (1982).
13. Mishra JK, Rao JS, Sastry GN, Panda G, Regioselective aminoethylation of 1,4- benzodiazepin-2-one under conventional heating and microwave irradiation, Tetrahedron Lett. 47, 3357 (2006).
14. Amayaly B, Jose LL, Judit A, Elena C, Eusebio J, Diastereoselective alkylation of a chiral 1,4-benzodiazepine-2,5-dione containing the a-phenethyl group: Attempted asymmetric synthesis of a,β- diaminopropionic acid, ARKIVOC (xii) 4 (2002).
15. Frederic F, Jana SOS, Sandrine FJ, Sylvain R, An expedient route to aromatic pyrrolo[2,1- c][1,4]benzodiazepines and a study of their reactivity, Tetrahedron Lett. 42, 5183 (2001).
16. Butcher JW, Liverton NJ, Selnick HG, Elliot JM, Smith GR, Tebben AJ, Pribush DA, Wai JS, Claremon DA, Preparation of 3-Amino-1,4-benzodiazepin-2-ones via Direct Azidation with Trisyl Azide, Tetrahedron Lett. 37, 6685 (1996).
17. Robert YN, Leo HS, Quinazolines and 1,4-Benzodiazepines. The Azido Group, Novel Pharmacophoric Substituent, 7- Azido-5-phenyl- 1,4-benzodiazepines, J. Med. Chem. 16, 8 (1973).
18. Malanciuc C, Arama C, Saramet I, Monciu C, Nedelcu A, Constantinescu C, Analytical characterization of flunitrazepam, Farmacia, 57, 2 (2009).
19. Naim HA, Khaled QS, Mohammad II, Sami HT, A facile synthesis of quinazolino[1,4]benzodiazepine alkaloids via reductive N-heterocyclization of N-(2- nitrobenzoyl)amides: Total synthesis of asperlicin C, circumdatin H, and analogues, ARKIVOC (ix) 282-292 (2010).
20. Lam PCH, Carlier PR, Experimental and computational studies of ring inversion if 1,4-benzodiazepin-2-ones: Implications for memory of chirality transformations, J. Org. Chem. 70, 1530 (2005).
21. Teresa GM, Cenarruzabeitia E, Del RJ, Herranz R, Versatile synthesis of chiral 2-substituted-5-oxo-1,2,3,4-tetrahydro- 5H-1,4-benzodiazepines as novel scaffolds for peptidomimetic building, Tetrahedron, 59, 4491 (2003).
22. MacQuarrie-Hunter S, Carlier PR, Highly enantioselective synthesis of rigid, quaternary 1,4-benzodiazepine-2,5- diones derived from proline, Org. Lett. 7, 5305 (2005).
23. Ottesen LK, Ek F, Olsson R, Ironcatalyzed cross-coupling of imidoyl chlorides with Grignard reagents, Org. Lett. 8, 1771 (2006).
24. Andrew PO, Alan N, Adam CT, Earl EC, Timothy H, Huw DL, Michael R, Jonathan DJ, Wrigley Jose LC, High Affinity, Bioavailable 3-Amino-1,4- benzodiazepine-Based-Secretase Inhibitors, Bioorg. Med. Chem. Lett. 13, 4143 (2003).
25. Dondas HA, Grigg R, Thornton-Pett M, Spiro(pyrrolidinyl-2,3'-benzodiazepines) Related to MK-329, Tetrahedron 52, 13455 (1996).
26. Despinoy C, Lloyd D, McNab H, Reed D, Flash Vacuum Pyrolysis of 1,5- Benzodiazepines, Tetrahedron, 54, 9667 (1998).
27. Sternbach LH, The benzodiazepine story, J. Med. Chem. 22, 1 (1979).
28. Cabedo N, Pannecoucke X, Quirion JC, An Efficient Asymmetric Synthesis of 2- Substituted 1,4-Benzodiazepin-3-one as a Potential Molecular Scaffold, Eur. J. Org. Chem. 8, 1590 (2005).
29. Rashid M, Mishra R, Husain A, Ahmad B, Synthesis of some novel C3 substituted new diazo-[1,4]-benzodiazepine-2-one derivatives as potent anticonvulsants, Chem. Sci. J. 5, 1 (2010).
30. Snider BB, Zeng H, Total synthesis of (-)- fumiquinazolines A, B, C, E, H, and I: Approaches to the synthesis of fiscalin A, J. Org. Chem. 68, 545 (2003).
31. Kamal A, Tekumalla V, Krishnan A, Pal- Bhadra M, Bhadra U, Development of pyrrolo[2,1-c][1,4]benzodiazepine galactoside prodrugs for selective therapy of cancer by ADEPT and PMT, Chem. Med. Chem. 3, 794 (2008).
32. Puvvada MS, Forrow SA, Hartley JA, Stephenson P, Gibson I, Jenkins TC, Thurston DE, Inhibition of bacteriophage T7 RNA polymerase in vitro transcription by DNA-binding pyrrolo[2,1- c][1,4]benzodiazepines, Biochemistry, 36, 2478 (1997).
33. Del Rio RE, Wang B, Achab S, Boche L, Highly enantioselective oxidation of sulphides to sulphoxides by a new oxaziridinium salt, Org. Lett. 9, 2265 (2007).
34. Singh H, Sattayasai J, Lattmann P, Boonprakob Y, Lattmann E, Antidepressant/Anxiolytic and Anti- Nociceptive Effects of Novel 2- Substituted 1,4-Benzodiazepine-2-ones, Sci. Pharm. 78, 155 (2010).
35. O'Neil IA, Thompson S, Kalindjian SB, Jenkins TC, The synthesis and biological activity of C2-fluorinated pyrrolo[2,1- c][1,4]benzodiazepines, Tetrahedron Lett. 44, 7809 (2003).
36. Wang T, Lui AS, Cloudsdale IS, A Novel Route to Pyrrolo[2,1- c][1,4]benzodiazepin-5-ones. Formal Total Synthesis of (+)-DC-81, Org. Lett. 1, 1835 (1999).
37. Fadia EA, Catherine CKY, Stephen TR, Leon BH, Regioselective alkylation at the N4 position of a 3-oxo-1,4- benzodiazepine on solid support, Molecular Diversity, 5, 1 (2000).
38. Juaristi E, Luis LRJ, Ramrez-Quiro Y, Enantioselective synthesis of amino acids from chiral 1,4-benzodiazepine-2,5- diones containing the phenethyl group, J. Org. Chem. 64, 2914 (1999).
39. Norman WG, Blount JF, Sternbach LH, Quinazolines and 1,4-benzodiazepines: the base-catalyzed rearrangement of 2- dimethylamino-5-phenyl-7-chlorol3h-l,4- benzodiazepine 4-oxide, J. Org. Chem. 37, 91 (1979).
40. Laura C, Ana CA, Cristina A, Davide B, Pyrrolo[2,1-c][1,4]benzodiazepine as a Scaffold for the Design and Synthesis of Anti-Tumour Drugs, Anti-Canc. Agents in Med. Chem. 9, 1 (2009).
41. Carlier PR, Lam PCH, DeGuzman J, Zhao H, Memory of chirality trapping of low inversion barrier 1,4-benzodiazepin- 2-one enolates, Tetrahedron: Asymmetry 2005, 16, 2998.
42. Branytska OV, Neumann R, An Efficient, Catalytic, Aerobic, Oxidative Iodination of Arenes Using the Polyoxometalate as Catalyst, J. Org. Chem. 68, 9510 (2003).
43. Malanciuc C, Arama C, Saramet I, Monciu CM, Florea M, Mihai NG, Contributions to the analytical study of midazolam, Farmacia, LVII, 1 (2009).
44. Rashid M, Husain A, Mishra R, Ahmad B, Synthesis and anti-anxiety activity of 7- chloro-5-phenyl-1,3-dihydro-1H, 3H-1,4- benzodiazepine-2-one derivatives in mice, Der. Pharmacia Lettre. 2, 253 (2010).
45. Robert YN, Fryer RI, Pradeep BM, Sluboski B, Reactions of Some Di-4- morpholinylphosphinyloxy Imines, J. Org. Chem. 41, 16 (1976).
46. Lam PCH, Ph.D. thesis, Virginia Polytechnic Institute and State University, Blacksburg VA, 2004.
47. Tracy DM, Jennifer B, Structurally Diagnostic Ion-Molecule Reactions and Collisionally Activated Dissociation of 1,4-Benzodiazepines in a Quadrupole Ion Trap Mass Spectrometer, Anal. Chem. 65, 2380 (2003).
48. Schwartz RH, Milteer R, Lebeau MA, Drug-facilitated sexual assault (date rape), Southern Med. J. 93, 6, 558 (2000).
49. Eric L, Jintana S, Pornthip L, David CB, Carl HS, Jordchai B, Wanchai A, Harjit S, Michael O, Alexander S, Anti-depressant and anti-nociceptive effects of 1,4- benzodiazepine-2-ones based cholecystokinin (CCK2) antagonists, Drug Discov. Ther. 1, 45 (2007).
50. Park YD, Kim HK, Kim JJ, Cho SD, Kim SK, Shiro M, Yoon YJ, N-nitration of secondary amines with 4-chloro-5- methoxy-2-nitropyridazin-3-one, J. Org. Chem. 68, 9113 (2003).
51. Ishizumi K, Mori K, Komeno Y, Katsube J, Yamamoto H, Japanese Patent 7739690, C. A. 87, 152287 (1977).
52. Karp GM, Palladium(II)-Mediated Coupling Reactions of Bromo- and Iodo- 1H-1,4-benzodiazepine-2,5-diones. A Route to Functionalized Benzodiazepinediones, J. Org. Chem. 60, 5814 (1995).
53. Hu WP, Wang JJ, Lin FL, Lin YC, Lin SR, Hsu MH, An efficient synthesis of pyrrolo[2,1-c][1,4]benzodiazepine. Synthesis of the antibiotic DC-81, J. Org. Chem. 66, 2881 (2001).
54. Iskra J, Stavber S, Zupan M, Nonmetal- Catalyzed Iodination of Arenes with Iodide and Hydrogen Peroxide, Synthesis, 26, 1869 (2004).
55. Cheng P, Zhang Q, Maa Y, Jiang Z, Zhang X, Zhang F, Chen J, Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloroquinolin-2-one and 5- aryl-7-chloro-1,4-benzodiazepine derivatives, Bioorg. Med. Chem. Lett. 18, 3787 (2008).
56. Katritzky AR, Mehta S, He HY, Syntheses of pyrrolo- and indoloisoquinolinones by intramolecular cyclizations of 1-(2-arylethyl)-5- benzotriazolylpyrrolidin-2-ones and 3- benzotriazolyl-2-(2-arylethyl)-1- isoindolinones, J. Org. Chem. 66, 148 (2001).
57. Katritzky AR, Xu YJ, He HY, Convenient synthesis of 2,3,4,5-tetrahydro-1,4- benzothiazepines, -1,4-benzoxazepines and -1,4-benzodiazepines, J. Chem. Soc. Perkin Trans 1, 592 (2002).
58. Pozo D, Macas A, Alonso E, Gonzalez J, Reactions of 1,4-Benzodiazepinic NNitrosoamidines with Tosylmethyl Isocyanide: A Novel Synthesis of Midazolam, Synthesis, 16, 2697 (2004).
59. Hu W, Tsai P, Hsu M, Wang J, Novel Borane Reduction of Ether-Protected Aromatic Lactams, J. Org. Chem. 69, 3983 (2004).
60. Chen BC, Sundeen JE, Guo P, Bednarz MS, Zhao R, Novel Triethylsilane Mediated Reductive N-Alkylation of Amines: Improved Synthesis of 1-(4- Imidazolyl)methyl-4- sulfonylbenzodiazepines, New Farnesyltransferase Inhibitors, Tetrahedron Lett. 42, 1245 (2001).
61. Kaname M, Tsuchiya T, Sashida H, Thermal Ring Contraction of 3H-1,4- Benzodiazepines into Quinazolines, Heterocycles, 51, 2407 (1999).
62. Le BG, Provot O, Bekaert A, Peyrat JF, Alami M, Brion JD, a-Iodination of Ketones, Synthesis, 9, 1537 (2006).
63. Carlos P, Alberto M, Fernando L, Miguel AM, Eduardo A, Javier G, Diastereo- and Enantioselective Synthesis of Novel β- Lactam-Containing 1,4-Benzodiazepines through a Ketene_Imine Cycloaddition Reaction, Eur. J. Org. Chem. 535 (2004).
64. Nadin A, Sanchez LJM, Owens AP, Howells DM, Talbot AC, Harrison T, New synthesis of 1,3-dihydro-1,4- benzodiazepin-2(2H)-ones and 3-amino- 1,3-dihydro-1,4-benzodiazepin-2(2H)- ones: Pd-catalyzed cross-coupling of imidoyl chlorides with organoboronic acids, J. Org. Chem. 68, 2844 (2003).
65. Maffrand JP, Ferrand G, Eloy F, Synthesis of 4H-imidazo[1,2-a]- benzodiazepines, Tetrahedron Lett. 36, 3449 (1973).