SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL EVALUATION OF SOME TETRAHYDROQUINAZOLINE DERIVATIVES OF BENZO[B]THIOPHENE
Abstract
In the present investigation, synthesis of 4-(1-(3-chlorobenzo[b]thiophene-2-carbonyl)-1H-indol-3-yl)-7, 7-dimethyl-3, 4, 7, 8-tetrahydroquinazoline2, 5(1H, 6H)dione (3a-d) is described. These unreported compounds are obtained starting from indole- 3-aldehyde and3-chloro-1benzothiophene-2-carbonylchloride (1a-d). A series of compounds (3a-d) were prepared. The structures of the newly synthesized compounds were elucidated on the basis of IR and 1H NMR spectral data of the compounds. All the compounds have been screened for antibacterial activity against S. aureus, E. coli, and P. aeruginosa and for antifungal activity against Candida albicans, A. niger, and A. clavatus using broth dilution method and they were found to exhibit good to moderate antimicrobial activity.
Keywords:
3-chlorobenzo[b]thiophene-2-carbonyl, Synthesis, Antimicrobial activityDOI
https://doi.org/10.25004/IJPSDR.2015.070507References
Singh K, Sharma VK. Synthesis and antimicrobial study of (Z)-5-(substituted benzylidene)-2-(benzo[b]thiophene-2-carbonyl)-3-phenyl-1, 2-dihydro-1, 2, 4-triazin-6(5H)-one. Asian Journal of Biochemical and Pharmaceutical Research 2014; 4(3): 179-186, 8.
Dang H, Chorell E, Uvell H, Pinkner JS, Hultgren SJ, Almqvist F. Syntheses and biological evaluation of 2-amino-3-acyl-tetrahydrobenzothiophene derivatives; antibacterial agents with antivirulence activity. Organic & Biomolecular Chemistry 2014; 12(12): 1942-1956.
Naganagowda G, Thamyongkit P, Petsom A. Synthesis and antimicrobial activities of benzothiophene derivatives. Journal of the Chilean Chemical Society 2012; 57(1): 1043-1047.
Vibhutimath GB, Mruthyunjayaswamy BHM. Synthesis and antimicrobial activity of some new N'-(3-chloro-6-substituted benzo[b]thiophene-2-carbonyl) substituted 2-oxo-2H-pyrano [2, 3-b] quinoline-3-carbohydrazides. Organic Chemistry: An Indian Journal 2011; 7(5): 325-331.
Shedid SAM, Hassan HM, Kora FA, El-Eisawy RM. Synthesis and antibacterial activity of some new amino acid derivatives of 3-chloro-6-(methyl)benzo[b]thiophene-2carboxylic acid. Journal of Chemical and Pharmaceutical Research 2011; 3(1): 388-394.
Isloor AM, Kalluraya B, Sridhar PK. Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives. European journal of medicinal chemistry 2010; 45(2): 825-30.
Guruprasad BV, Mruthyunjayaswamy BHM. Synthesis and antimicrobial activity of some new 3-chloro-6-substituted-N-(substituted 2H-[1,3]oxazino[6,5-b]quinolin3-(4H,5aH,9aH)-yl)benzo[b]thiophene-2-carboxamides. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry 2012; 51B(3): 514520.
Tirlapur VK, Swamy KM, Prasad YR. Synthesis and antimicrobial studies of substituted benzo[b]thiophenes and their derivatives. International Journal of Chemical Sciences 2008; 6(4): 2008-2015.
Pinto E, Queiroz Maria-Joao RP, Vale-Silva LA, Oliveira JF, Begouin A, Begouin Jeanne-M, Kirsch G. Antifungal activity of synthetic di(hetero)arylamines based on the benzo[b]thiophene moiety. Bioorganic & Medicinal Chemistry 2008; 16(17): 8172-8177.
Yadav PP, Gupta P, Chaturvedi AK, Shukla PK, Maurya R. Synthesis of 4-hydroxy-1-methylindole and benzo[b]thiophen-4-ol based unnatural flavonoids as new class of antimicrobial agents. Bioorganic & Medicinal Chemistry 2005; 13(5): 1497-1505.
Tanaka J, Yuasa T, Kawakami Y, Terajima K, Ishizuka Y. Preparation of antifungal triazole-containing 2,3-dihydrobenzo[b]thiophene derivative. Jpn. Kokai Tokkyo Koho. 1996; JP 08253475 A 19961001.
Drouhet E, Dupont B. In vitro antifungal activity of sertaconazole. Arzneimittel-Forschung. 1992; 42(5A): 705-10.
Boyd JE, Sommerville RG. Antiviral activity of some related benzo(b) thiophene derivatives. I. Initial screening tests. Archiv fuer die Gesamte Virusforschung. 1974; 45(3): 249-53.
Shimizu S, Hosoya T, Murohashi M, Yoshida S. Benzothiophene compound, alternative autophagy-inducing agent and anticancer drug including benzothiophene compound as active ingredient, and method for screening for compounds having anticancer activity. PCT Int. Appl. 2013; WO 2013118842 A1 20130815.
Penthala NR, Sonar VN, Horn J, Leggas M, Yadlapalli Jai Shankar KB, Crooks PA. Synthesis and evaluation of a series of benzothiophene acrylonitrile analogs as anticancer agents. Med Chem Comm. 2013; 4(7): 1073-1078.
Kagatani S, Odanaka J, Kano H. DNA methyltransferase inhibitors and antitumor agents containing benzo[b]thiophene derivatives. Jpn. Kokai Tokkyo Koho. 2007; JP 2007153792 A 20070621.
Li Z, Liu K. Preparation of benzo[b]thiophene derivatives as anti-inflammatory agents. Faming Zhuanli Shenqing. 2013; CN 103058988 A 20130424.
Lakshmeesha CS, Venugopala Reddy KR, Mohan S. Synthesis and microwave assisted transformation of ethyl-4,5,6,7-tetrahydro benzo (b) thiophene-2-amino-3-carboxylate into potential anti-inflammatory agents- novel mono and diacids. Archives of Applied Science Research 2011; 3(5): 556-561.
Gouda, TS, Jagadish, Salahuddin, M Shantakumar SM. Synthesis and antiinflammatory activity of some novel benzo(b)thiophene substituted thiazolidinones. Asian Journal of Chemistry 2009; 21(7): 5171-5178.
Radwan Mohamed AA, Shehab MA, El-Shenawy SM. Synthesis and biological evaluation of 5-substituted benzo[b]thiophene derivatives as anti-inflammatory agents. Monatshefte fuer Chemie. 2009; 140(4): 445-450.
Fakhr IMI, Radwan MAA, El-Batran S, Abd El-Salam Omar ME, El-Shenawy SM. Synthesis and pharmacological evaluation of 2-substituted benzo[b]thiophenes as anti-inflammatory and analgesic agents. European Journal of Medicinal Chemistry 2009; 44(4): 1718-1725.
Svoboda J, Stadler M, Jandera A, Panajotova V, Kuchar M. Synthesis and biological evaluation of new antiinflammatory 1-benzothiophene-2-carboxanilides. Collection of Czechoslovak Chemical Communications 2000; 65(7): 1082-1092.
Yoshid, Y. Preparation of benzo[b]thiophene-2-carboxylic acids as intermediates for anti-inflammatory and antiallergy agents. Jpn. Kokai Tokkyo Koho. 1993; JP 05194484 A 19930803.
Banerjee T, Kapoor N, Surolia N, Surolia A. Benzothiophene carboxamide derivatives as novel antimalarials. IUBMB Life. 2011; 63(12): 1111-1115.
Bhatt R, Sharma S, Patidar AK, Rathore KK, Senwar RC, Dashora R, Mehta A. Synthesis and Antimicrobial evalution of some imidazo imidazole Pyrimidines derivatives of benzo[b]thiophene. Inter. J. of Pharmacy and Pharma. Sci. Res. 2015; 5(1): 8-12.
Nagesh HK, Padmashali B, C. Sandeep, T.C.M. Yuvaraj, M.B. Siddesh, S. M. Mallikarjuna. Synthesis and Antimicrobial Activity of Benzothiophene Substituted Coumarins, Pyrimidines and Pyrazole as New Scaffold. Int. J. Pharm. Sci. Rev. Res. 2014; 28(2): 6-10.
Vivekanand D, Biradarand BHM, Mruthyunjayaswamy. Synthesis Characterization and Antimicrobial Activity Studies of Some Transition Metal Complexes Derived from 3-Chloro-N-[(1E)-(2-hydroxy phenyl)methylene]-6methoxy-1-benzothiophene-2-carbohydrazide. Hindawi Publishing Corporation. The Scientific World Journal 2013; Article ID 451629: 13.
Singh A, Singh SP, Amalraj A, Gokulan PD, Porwal P. Synthesis, Characterization and Biologial Evaluation of 2-amino-3-(n-cyclohexyl carboxamido)- 4,5,6,7-tetrahydrobenzo (b) Thiophine Derivatives. Inter. J. of Pharma. & Bio. Archives. 2011; 2(1): 534-540.
Vasoya SL, Paghdar DJ, Chovatia PT, Joshi HS. Synthesis of some New Thiosemicarbazide and 1,3,4Thiadiazole Heterocycles Bearing Benzo[b]Thiophene Nucleus as a Potent Antitubercular and Antimicrobial Agents. J. of Sci., Islamic Republic of Iran 2001; 16(1): 33-36.
Thakar KM, Paghdar DJ, Chovatia PT and Joshi HS. Synthesis of thiourea derivatives bearing the benzo[b]thiophene nucleus as potential antimicrobial agents. J. Serb. Chem. Soc. 2005; 70 (6): 807-815.
Kumara THS, Mahadevan KM, Harishkumar HN, Padmashali B, Naganagowda G. Synthesis of benzo[b]thiophene substituted carbamates, ureas, semicarbazides, and pyrazoles and their antimicrobial and analgesic activity. Phosphorus, Sulfur and Silicon and the Related Elements 2009; 184(7):1866-1879.
Published
Abstract Display: 605 
PDF Downloads: 826 
