Synthesis, antimicrobial and DNA cleavage studies of some 4-aryloxymethylcoumarins obtained by reaction of 4-bromomethylcoumarins with bidentate nucleophiles

Medicinal Chemistry Research

Volumn 21, Issue 9, 2012, Pages 2603-2614

  Makandar, Shabana Banu N ^a,b   Basanagouda, Mahantesha ^a   Kulkarni, Manohar V ^a   Pranesha, ^c   Rasal, Vijaykumar P ^c  

^a KARNATAK UNIVERSITY   (India)

^b SDM COLLEGE OF ENGINEERING AND TECHNOLOGY   (India)

^c K L E S S COLLEGE OF PHARMACY   (India)

Author keywords

3 Aminophenol; 3 Diethylaminophenol; Coumarin; DNA; Microbial; Resorcinol

Indexed keywords

1 (3 HYDROXY PHENOXYMETHYL)BENZO(F)COUMARIN; 4 (3 DIETHYLAMINO PHENOXYMETHYL) 6 METHYL COUMARIN; 4 (3 DIETHYLAMINO PHENOXYMETHYL) 7 METHYL COUMARIN; 4 (3 HYDROXY PHENOXYMETHYL) 6 BROMOCOUMARIN; 4 (3 HYDROXY PHENOXYMETHYL) 6 CHLOROCOUMARIN; 4 (3 HYDROXY PHENOXYMETHYL) 6 METHOXYCOUMARIN; 4 (3 HYDROXY PHENOXYMETHYL) 6 METHYLCOUMARIN; 4 (3 HYDROXY PHENOXYMETHYL) 7 METHYLCOUMARIN; 4 (3 HYDROXY PHENOXYMETHYL)BENZO(H)COUMARIN; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; BIS[(4 PHENOXYMETHYL) 6 BROMOCOUMARIN]; BIS[(4 PHENOXYMETHYL) 6 CHLOROCOUMARIN]; BIS[(4 PHENOXYMETHYL) 6 METHOXYCOUMARIN]; BIS[(4 PHENOXYMETHYL) 6 METHYLCOUMARIN]; BIS[(4 PHENOXYMETHYL) 7 METHYLCOUMARIN]; BIS[(4 PHENOXYMETHYL)BENZO(F)COUMARIN]; BIS[(4 PHENOXYMETHYL)BENZO(H)COUMARIN]; CIPROFLOXACIN; COUMARIN DERIVATIVE; FLUCONAZOLE; N [3 (6 BROMO COUMARIN 4 YLMETHOXY)PHENYL]ACETAMIDE; N [3 (6 CHLORO COUMARIN 4 YLMETHOXY)PHENYL]ACETAMIDE; N [3 (6 METHOXY COUMARIN 4 YLMETHOXY]PHENYL]ACETAMIDE; N [3 (6 METHYL COUMARIN 4 YLMETHOXY)PHENYL]ACETAMIDE; N [3 (7 METHYL COUMARIN 4 YLMETHOXY)PHENYL]ACETAMIDE; N [3 [2H BENZO(H)COUMARIN 4 YLMETHOXY]PHENYL]ACETAMIDE; N [3 [3H BENZO(F)COUMARIN 1 YLMETHOXY]PHENYL]ACETAMIDE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FUMIGATUS; ASPERGILLUS NIGER; BACILLUS SUBTILIS; BACTERIAL STRAIN; CANDIDA ALBICANS; CHEMICAL REACTION; COMPETITIVE INHIBITION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DISK DIFFUSION; DNA CLEAVAGE; DNA SYNTHESIS; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; FUSARIUM OXYSPORUM; GEL ELECTROPHORESIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PENICILLIUM CHRYSOGENUM; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; ROOM TEMPERATURE; STAPHYLOCOCCUS AUREUS;

EID: 84866403066     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9785-z     Document Type: Article

References (39)

1. Appendino G, Mercalli E, Fuzzati N, Arnoldi L, Stavri M, Gibbons S, Ballero M, Maxia A (2004) Antimycobacterial coumarins from the sardinian giant fennel (ferula communis). J Nat Prod 67:2108-2110 (Pubitemid 40092568)
2. Basanagouda M, Kulkarni MV, Sharma D, Gupta VK, Pranesha, Sandhyarani P, Rasal VP (2009) Synthesis of some new 4-aryloxymethylcoumarins and examination of their antibacterial and antifungal activities. J Chem Sci 122:485-495
3. Basanagouda M, Shivashankar K, Kulkarni MV, Rasal VP, Patel H, Mutha SS, Mohite AA (2010) Synthesis and antimicrobial studies on novel sulfonamides containing 4-azidomethyl coumarin. Eur J Med Chem 45:1151-1157
4. Bedoya LM, Beltran M, Sancho R, Olmedo DA, Sanchez-Palomino S, del Olmo E, Lopez-Perez JL, Munoz E, Feliciano AS, Alcami J (2005) 4-Phenylcoumarins as HIV transcription inhibitors. Bioorg Med Chem Lett 15:4447-4450 (Pubitemid 41253872)
5. Binda C, Wang J, Pisan L, Caccia C, Carotti A, Salvati P, Edmondson DE, Mattevi A (2007) Structures of human monoamine oxidase B complexes with selective noncovalent inhibitors: safinamide and coumarin analogs. J Med Chem 50:5848-5852 (Pubitemid 350106038)
6. Brown TA (1990) Essential molecular biology: a practical approach, vol 1. IRL Press, Oxford, UK pp 51-52
7. Burger A, Ullyot GE (1947) Analgesic studies. β-ethyl and β-isopropylamine derivatives of pyridine and thiazole. J Org Chem 12:342-355
8. Catto M, Nicolotti O, Leonetti F, Carotti A, Favia AD, Otero RS, Mndez-lvarez E, Carotti A (2006) Structural insights into monoamine oxidase inhibitory potency and selectivity of 7-substituted coumarins from ligand- and target-based approaches. J Med Chem 49:4912-4925 (Pubitemid 44201049)
9. Cruickshank R, Duguid JP, Marion BP, Swain RHA (1975) Medicinal microbiology, vol 1, 12th edn. Churchil Livingstone, London, pp 196-202
10. Durairaj RB (2005) Textbook: resorcinol: chemistry, technology and applications. Springer-Verlag, Berlin Heidelberg, Printed in Germany
11. Fylaktakidou KC, Hadjipavlou-Latina DJ, Litinas KE, Nicolaides DN (2004) Natural and synthetic coumarin derivatives with antiinflammatory/antioxidant activities. Curr Pharm Design 10: 3813-3833 (Pubitemid 39409872)
12. Ghate MD, Kulkarni MV, Shobha R, Kattimani SY (2003) Synthesis of vanillin ethers from 4-(bromomethyl) coumarins as antiinflammatory agents. Eur J Med Chem 38:297-302 (Pubitemid 36349672)
13. Gnerre C, Catto M, Leonetti F, Weber P, Carrupt PA, Altomare C, Carotti A, Testa B (2000) Inhibition of monoamine oxidases by functionalized coumarin derivatives: biological activities, QSARs, and 3D-QSARs. J Med Chem 43:4747-4758 (Pubitemid 32002686)
14. Halterman RL, Martyn DE (2007) Translational isomerizations in [2]catenanes with unsymmetrically substituted resorcinol-based tethers. J Org Chem 72:7841-7848 (Pubitemid 47582567)
15. Ito C, Itoigawa M, Mishina V, Filho VC, Enjo F, Tokuda H, Nishino H, Furukawa H (2003) Chemical constituents of Calophyllum brasiliense. 2. Structure of three new coumarins and cancer chemopreventive activity of 4-substituted coumarins. J Nat Prod 66:368-371 (Pubitemid 36384013)
16. Jadhav VB, Nayak SK, Guru Row TN, Kulkarni MV (2010) Synthesis, structure and DNA cleavage studies of coumarin analogues of tetrahydroisoquinoline and protoberberine alkaloids. Eur J Med Chem 45:3575-3580
17. Khan ZK (1997) In vitro and in vivo screening techniques for bioactivity screening and evaluation. In: Proceedings of international workshop UNIDO-CDRI, pp. 210-211
18. Khan KM, Saify ZS, Khan MZ, Ullah Z, Choudhary MI, Rahman AU, Perveen S, Chohan ZH, Supuran CT (2004) Synthesis of coumarin derivatives with cytotoxic, antibacterial and antifungal activity. J Enz Inhib Med Chem 19:373-379 (Pubitemid 39172903)
19. Kirkiacharian S, Thuy DT, Sicsic S, Bakhchinian R, Kurkjian R, Tonnaire T (2002) Structure-activity relationships of some 3-substituted-4- hydroxycoumarins as HIV-1 protease inhibitors. Farmaco 57:703-708 (Pubitemid 35299380)
20. Kontogiorgis CA, Litina DH (2004) Synthesis and biological evaluation of novel coumarin derivatives with a 7-azomethine linkage. Bioorg Med Chem Lett 14:611-614 (Pubitemid 38114837)
21. Kontogiorgis CA, Litina DH (2005) Synthesis and antiinflammatory activity of coumarin derivatives. J Med Chem 48:6400-6408 (Pubitemid 41428992)
22. Kontogiorgis CA, Sowoglou K, Hadjipavlou-Litina DJ (2006) Antiinflammatory and antioxidant evaluation of novel coumarin derivatives. J Enz Inhib Med Chem 21:21-29 (Pubitemid 43884197)
23. Kulkarni MV, Patil VD (1981) Studies on coumarins I. Arch Pharm (Weinheim) 314:708-711
24. Kulkarni MV, Kulkarni GM, Lin CH, Sun CM (2006) Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents. Curr Med Chem 13:2795-2818 (Pubitemid 44509726)
25. Lee KH (2004) Current developments in the discovery and design of new drug candidates from plant natural product leads. J Nat Prod 67:273-283
26. Lee BH, Clothier MF, Dutton FE, Conder GA, Johnson SS (1998) Anthelmintic β-hydroxyketoamides (BKAs). Bioorg Med Chem Lett 8:3317-3320
27. Manvar A, Malde A, Verma J, Virsodia V, Mishra A, Upadhyay K, Acharya H, Coutinho E, Shah A (2008) Synthesis, antitubercular activity and 3D-QSAR study of coumarin-4-acetic acid benzylidene hydrazides. Eur J Med Chem 43:2395-2403
28. Marsini MA, Huang Y, Van De Water RW, Pettus TRR (2007) Synthesis of resorcinol derived spironitronates. Org Lett 9:3229-3232
29. Nicolaides DN, Fylaktakidou KC, Litinas KE, Litina DH (1998) Synthesis and biological evaluation of several coumarin-4-carboxamidoxime and 3-(coumarin-4-yl)-1, 2, 4-oxadiazole derivatives. Eur J Med Chem 33:715-724 (Pubitemid 29161321)
30. Raj HG, Parmar VS, Jain SC, Goel S, Pooman Himanshu, Malhotra S, Singh A, Olsen CE, Wengel J (1998) Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part I: dioxygenated 4-methyl coumarins as superb antioxidant and radical scavenging agents. Bioorg Med Chem 6:833-839 (Pubitemid 28287285)
31. Roma G, Braccio MD, Grossi G, Piras D, Leoncini G, Bruzzese D, Signorello MG, Fossa P, Mosti L (2007) Synthesis and in vitro antiplatelet activity of new 4-(1-piperazinyl)coumarin derivatives. Human platelet phosphodiesterase 3 inhibitory properties of the two most effective compounds described and molecular modeling study on their interactions with phosphodiesterase 3A catalytic site. J Med Chem 50:2886-2895 (Pubitemid 46980859)
32. Shastri LA, Kulkarni MV (2004) Dual fluorescence and biological evaluation of paracetamol ethers from 4-bromomethyl-coumarins. Ind J Chem 43B:2416-2422 (Pubitemid 40186507)
33. Silvan AM, Abad MJ, Bermejo P, Sollhuber M, Villar A (1996) Antiinflammatory activity of coumarins from Santolina oblongifolia. J Nat Prod 59:1183-1185 (Pubitemid 27026586)
34. Stanchev S, Momekov G, Jensen F, Manolov I (2008) Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives. Eur J Med Chem 43:694-706 (Pubitemid 351447326)
35. Stanchev S, Hadjimitova V, Traykov T, Boyanov T, Manolov I (2009) Investigation of the antioxidant properties of some new 4-hydroxycoumarin derivatives. Eur J Med Chem 44:3077-3082
36. Thaisrivongs V, Tomich PK, Watenpaugh KD (1994) Structure based design of HIV protease inhibitors: 4-hydroxycoumarins and 4-hydroxy-2-pyrones as non-peptidic inhibitors. J Med Chem 37:3200-3204 (Pubitemid 24325031)
37. Tocco G, Fais A, Meli G, Begala M, Podda G, Fadda MB, Corda M, Ataña'is OA, Filippone P, Berretta S (2009) PEG-immobilization of cardol and soluble polymer-supported synthesis of some cardol-coumarin derivatives: preliminary evaluation of their inhibitory activity on mushroom tyrosinase. Bioorg Med Chem Lett 19:36-39
38. Trenor SR, Shultz AR, Love BJ, Long TE (2004) Coumarins in polymers: from light harvesting to photo-cross-linkable tissue scaffolds. Chem Rev 104:3059-3077
39. Yadav GD, Badure OV (2008) Engineering selectivity in novel synthesis of 3-(phenylmethoxy)phenol from resorcinol and benzyl chloride under liquid-liquid-liquid phase transfer catalysis. Org Process Res Dev 12:755-764