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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 52, Number 3
JKCSEZ 52(3)
June 20, 2008 

Synthesis and Antibacterial Activity of New Tetrazole Derivatives

새로운 Tetrazole유도체의 합성과 항균활성
V. V. Mulwad*, Rupesh B Pawar,Atul C Chaskar

V. V. Mulwad*, Rupesh B Pawar, and Atul C Chaskar
4-하이드록시 쿠마린, knoevenegal 축합반응, 1.3 dipolar 반응, 항균활성 , 4-hydroxy Coumarin, Knoevenegal Condensation, 1,3 Dipolar Reaction, Antibacterial Activity
3-Acetyl/Formyl 4-hydroxy-2H(1)-benzopyran-2-one를 malonitrile와 ethyl cyanoacetate로 처리하여 각각 1,1-dicyano-2-[4/-hydroxy-2/H(1)-benzopyran-2/-one-3/-yl] ethene/propene 2a-h와 ethyl-2-cyano-3-[4/-hydroxy-2/H (1)-benzopyran-2/-one-3/-yl] propenoate/butenoate 3a-h를 얻었다. NaN3와 2a-h의 1.3 dipolar 반응에서 4a-h인 tetrazole유도체를 얻었다. 3a-h는 PPA를 이용한 고리화 반응으로 3-cyano-2H,5H-pyrano [3, 2-c] benzopyran-2,5- diones 5a-h를 얻었다. 5a-h는 NaN3와1.3 dipolar 반응으로 -(1/H-tetrazol-5/-yl)-2H,5H-pyrano[3, 2-c] benzopyran- 2,5-diones 6a-h얻었다. 화합물의 구조는 스펙트럼과 자료 분석을 기초로 입증했다.모든 화합물은 항균 활성을 검사하였 고 의미있는 항균성을 가짐을 밝혔다. 2h화합물과 4h 화합물은 50 μg/mL에서 활성을 보였다

3-Acetyl/Formyl 4-hydroxy-2H(1)-benzopyran-2-one on treatment with malonitrile and ethyl cyanoacetate yielded 1,1-dicyano-2-[4/-hydroxy-2/H(1)-benzopyran-2/-one-3/-yl] ethene/propene 2a-h and ethyl-2-cyano-3-[4/- hydroxy-2/H (1)-benzopyran-2/-one-3/-yl] propenoate/butenoate 3a-h respectively. The 1,3 dipolar reaction of 2a-h with NaN3 gave the tetrazole derivative 4a-h. 3a-h on cyclization with PPA gave 3-cyano-2H,5H-pyrano [3, 2-c] benzopyran- 2,5-diones 5a-h which on 1,3 dipolar reaction with NaN3 to gave 3-(1/H-tetrazol-5/-yl)-2H,5H-pyrano[3, 2-c] benzopyran- 2,5-diones 6a-h. The structures of the compounds have been established on the basis of the spectral and analytical data. All the compounds were screened for their antimicrobial activities and have been found to exhibited significant antibacterial activities. Compounds 2h and 4h showed the activity 50μg/mL.

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