Synthesis of β-amino carbonyl derivatives of coumarin and benzofuran and evaluation of their biological activity

Medicinal Chemistry Research

Volumn 22, Issue 10, 2013, Pages 4787-4797

  Kenchappa, R ^a   Bodke, Yadav D ^a   Peethambar, S K ^a   Telkar, Sandeep ^a   Bhovi, Venkatesh K ^a  

^a KUVEMPU UNIVERSITY   (India)

Author keywords

amino ketones; Antimicrobial; Antioxidant; Cerric ammonium nitrate; Glucosamine 6 phosphate synthase

Indexed keywords

1 ( 1 BENZOFURAN 2 YL) 3 ( 4 METHOXYPHENYL) 3 (PHENYLAMINO)PROPAN 1 ONE; 1 ( 1 BENZOFURAN 2 YL) 3 PHENYL 3 (PHENYLAMINO)PROPAN 1 ONE; 3 [ 3 PHENYL 3 (PHENYLAMINO)PROPANOYL 2H CHROMEN 2 ONE; 4 [ 3 (BENZOFURAN 2 YL) 1 ( 4 (DIMETHYLAMINO)PHENYL 3 OXO PROPYLAMINO]BENZOIC ACID; 4 [ 3 (BENZOFURAN 2 YL) 1 ( 4 CHLOROPHENYL) 3 OXOPROPYLAMINO]BENZOIC ACID; 4 [ 3 (BENZOFURAN 2 YL) 1 ( 4 METHOXYPHENYL) 3 OXOPROPYLAMINO]BENZOIC ACID; 4 [ 3 (BENZOFURAN 2 YL) 1 ( 4 METHYLPHENYL) 3 OXOPROPYLAMINO]BENZOIC ACID; 4 [ 3 (BENZOFURAN 2 YL) 1 ( 4 NITROPHENYL) 3 OXOPROPYLAMINO]BENZOIC ACID; 4 [[ 1 ( 4 CHLOROPHENYL) 3 OXO 3 ( 2 OXO 2H CHROMEN 3 YL)PROPYL]AMINO]BENZOIC ACID; 4 [[ 1 ( 4 DIMETHYLAMINOPHENYL) 3 OXO 3 ( 2 OXO 2H CHROMEN 3 YL)PROPYL]AMINO]BENZOIC ACID; 4 [[ 1 ( 4 FLUOROPHENYL) 3 OXO 3 ( 2 OXO 2H CHROMEN 3 YL)PROPYL]AMINO]BENZOIC ACID; 4 [[ 1 ( 4 METHOXYPHENYL) 3 OXO 3 ( 2 OXO 2H CHROMEN 3 YL)PROPYL]AMINO]BENZOIC ACID; 4 [[ 1 ( 4 METHYLPHENYL) 3 OXO 3 ( 2 OXO 2H CHROMEN 3 YL)PROPYL]AMINO]BENZOIC ACID; 4 [[ 1 ( 4 NITROPHENYL) 3 OXO 3 ( 2 OXO 2H CHROMEN 3 YL)PROPYL]AMINO]BENZOIC ACID; 4 [[ 3 ( 1 BENZOFURAN 2 YL) 1 ( 4 FLUOROPHENYL) 3 OXOPROPYL]AMINO]BENZOIC ACID; 4 [[ 3 ( 1 BENZOFURAN 2 YL) 3 OXO 1 PHENYLPROPYL]AMINO]BENZOIC ACID; 4 [[ 3 OXO 3 ( 2 OXO 2H CHROMEN 3 YL) 2 PHENYLPROPYL]AMINO]BENZOIC ACID; ALDEHYDE DERIVATIVE; AMMONIUM NITRATE; ANTIBIOTIC AGENT; AROMATIC AMINE; BENZOFURAN DERIVATIVE; CARBONYL DERIVATIVE; CERRIC AMMONIUM NITRATE; COUMARIN DERIVATIVE; FLUCONAZOLE; GLUTAMINE FRUCTOSE 6 PHOSPHATE AMINOTRANSFERASE; SCAVENGER; STREPTOMYCIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BACTERIAL STRAIN; BINDING AFFINITY; CATALYST; CHELATION; COMPUTER MODEL; CONTROLLED STUDY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVE SITE; FUNGAL STRAIN; IN VITRO STUDY; MANNICH REACTION; MICROBIAL ACTIVITY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; NONHUMAN; SCAVENGING SYSTEM; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 84883466254     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0494-7     Document Type: Article

References (28)

1. Abdel-Wahab BF, Abdel-Aziz HA, Ahmed EM (2009) Synthesis and antimicrobial evaluation of 1-(benzofuran-2-yl)-4-nitro-3-arylbutan-1-ones and 3-(benzofuran-2-yl)-4,5-ihydro-5-aryl-1-[4-(aryl)-1,3-thiazol-2-yl] -1H-pyrazoles. Eur J Med Chem 26:32-35
2. Ansari KF, Lal C (2009) Synthesis, physicochemical properties and antimicrobial activity of some new benzimidazole derivatives. Eur J Med Chem 44:4028-4033
3. Basawaraj R, Yadav B, Sangapure SS (2001) Synthesis of some 1H-pyrazolines bearing benzofuran as biologically active agents. Ind J Heterocycl Chem 11:31-34
4. Binkowski A, Naghibzadeg S, Liang J (2003) CASTp computed atlas of surface topography of proteins. Nucleic Acid Res 31:3352-3355
5. Braca A, Tommasi ND, Bari LD, Pizza C, Politi M, Morelli I (2001) New diterpenes from Jatropha divaricata. J Nat Prod 64:892-895
6. Chandrashekar A, Eswarappa B, Bodke YD, Venkatesh KB, Raghu N, Shivakumar MC, Peethambar SK, Telkar S (2012) 5-phenyl-1-benzofuran-2-yl derivatives: synthesis, antimicrobial, and antioxidant activity. Med Chem Res. doi: 10.1007/s00044-012-0017-y
7. Dawood KM, Abdel-Gawad H, Rageb EA, Ellithey M, Mohamed HA (2006) Synthesis, anticonvulsant, and anti-inflammatory evaluation of some new benzotriazole and benzofuran-based heterocycles. Bioorg Med Chem 14:3672-3680
8. Deepika S, Balasubramanian N, Pradeep Kumar, Vikramjeet J, Rakesh N, Erik DC, Jan B (2009) Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives. Eur J Med Chem 44:2347-2353
9. Elmastaş M, Gülçin I, Işildak Ö, Küfrevioǧlu ÖI, Ibaoǧlu K, Aboul-Enein HY (2006) Radical scavenging activity and antioxidant capacity of bay leaf extracts. J Iran Chem Soc 3:258-266
10. Hoult JRS, Paya M (1996) Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. Gen Pharmacol 27:713-722
11. Kennedy RO, Thornes RD (1997) Coumarins. Biology, applications and mode of action. Wiley, New York, pp 255-265
12. Mazaahir K, Divya B, Neeraj KM, Vikas B (2008) CAN catalyzed synthesis of β-amino compounds via Mannich reaction in PEG. Catal Commun 9:2547-2549
13. Melagraki G, Afantitis A, Markopoulou OI, Detsi A, Koufaki M, Kontogiorgis C, Hadjipavlou-Litina DJ (2009) Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts. Eur J Med Chem 44:3020-3026
14. Muller R, Goesmann H, Waldmann H (1999a) N,N-Phthaloylamino acids as chiral auxiliaries in asymmetric mannich-type reactions. Angew Chem 111:166-169
15. Muller R, Goesmann H, Waldmann H (1999b) N,N-Phthaloylamino acids as chiral auxiliaries in asymmetric mannich-type reactions. Angew Chem Int Ed 38:184-187
16. Nasser Khalil SAM (2010) Efficient synthesis of novel 1,2,4-triazole fused acyclic and 21-28 membered macrocyclic and/or lariat macrocyclic oxaazathia crown compounds with potential antimicrobial activity. Eur J Med Chem 45:5265-5277
17. Nevcihan G, Cengiz S, Bektas T, Halil SM (2010) Evaluation of antioxidant activities of 3 Edible mushrooms; Ramaria flava, Rhizopogan roseolusand Russula delica. Food Sci Biotech 19(3):691-696
18. Sandhya B, Giles D, Vinod M, Basavarajaswamy G, Rekha A (2011) Synthesis, pharmacological evaluation and docking studies of coumarin derivatives. Eur J Med Chem 46:4696-4701
19. Sharma P, Rane N, Gurram VK (2004) Synthesis and QSAR studies of pyramidal [4,5-d] Pyrididine-2,5-dione derivatives as potential antimicrobial agents. Bioorg Med Chem Lett 14:4185-4190
20. Sheelavanth S, Bodke YD, Sundar SM (2012) Synthesis, antioxidant, and antibacterial studies of phenolic esters and amides of 2-(1-benzofuran-2-yl) quinoline-4-carboxylic acid. Med Chem Res. doi: 10.1007/s00044-012-0117-8
21. Silvia NL, María VC, Susana AZ, José ND, Gricela L, Jaime CC, Juan CGC, Juan CR, Cristina D, Ana MR, Ricardo DE (2001) In vitro antifungal evaluation and structure-activity relationships of a new series of chalcone derivatives and synthetic analogues, with inhibitory properties against polymers of the fungal cell wall. Bioorg Med Chem 9:1999-2013
22. Sridharan V, Menendez JC (2010) Cerium (IV) ammonium nitrate as a catalyst in organic synthesis. Chem Rev. doi: 10.1021/cr100004p,110:3805-3849
23. Venkatesh KB, Bodke YD, Biradar SA (2010) Synthesis of 3-[4-(1-Benzofuran-2-yl)-1,3-thiazol-2-yl]-2-(4-aryl)-1,3-thiazolidin-4-one derivatives as biological agents. hosphorus. Sulfur Silicon 185:1926-1931
24. Vijesh AM, Isloor AM, Vivek P, Shaoib A, Shridhar M (2010) Synthesis, characterization and anti-microbial studies of some novel 2,4-disubstituted thiazoles. Eur J Med Chem 45:5460-5464
25. Wallace AC, Laskowski RA, Thornton JM (1995) LIGPLOT: a program to generate schematic diagrams of protein-ligand interactions. Prot Eng 8:127-134
26. Wang Hong-Juan, Mo Li-Ping, Zhang Zhan-Hui (2011) Cerium ammonium nitrate-catalyzed multicomponent reaction for efficient synthesis of functionalized tetrahydropyridines. ACS Comb Sci 13:181-185
27. Yuan YV, Bone DE, Carrington MF (2005) Antioxidant activity of dulse (Palmaria palmata) extractev aluated invitro. Food Chem 91:485-494
28. Yuefen Z, Zhongxiang S, Jamie MF, Thomas H, Daniel W (2006) Structure-activity relationships of novel antibacterial translation inhibitors: 3,5-diamino-piperidinyl triazines. Bioorg Med Chem Lett 16:5451-5456