Green, unexpected synthesis of bis-coumarin derivatives as potent anti-bacterial and anti-inflammatory agents
Abstract A green and efficient protocol has been developed and a series of coumarin based pyrano[3,2- c ]chromene derivatives ( 2 ) have been synthesized using multi-component reaction (MCR) approach. Unexpected 3-coumarinyl-3-pyrazolylpropanoic acids ( 3 ) and C 4 -C 4 chromenes ( 5 ) have been isolated instead of expected product 4 by the reaction of compound ( 2 ) in formic acid at 90 °C for about 4–5 h and at 130 °C for about 8–10 h respectively. Further, C 4 -C 4 chromenes ( 5 ) formation was confirmed by intramolecular cyclization of compounds ( 3 ). These compounds were screened for their biological activities and most of them exhibited promising antibacterial activity. The anti-inflammatory assay was evaluated against HRBC membrane stabilization method and the compounds exhibit excellent anti-inflammatory activity. Molecular docking study has been performed for all the synthesized compounds with Klebsiella pneumoni ae acetolactate synthase and results obtained are quite promising. Highlights Synthesis of coumarin based pyrano[3,2- c ]chromene derivatives were achieved in good to excellent yields underone-pot three component green method. The unexpected 3-coumarinyl-3-pyrazolylpropanoic acids (3) and C 4 -C 4 chromene derivatives (5) have been isolated by the reaction of compound (2) in acidic conditions. All the newly synthesized polyfunctionalized coumarin based pyrano[3,2- c ]chromenes are potent antibacterial and anti-inflammatory agents compared to standard. The molecular docking study reveals that, all newly synthesized polyfunctionalized coumarin based pyrano[2,3- c ]pyrazoles are well supported for invitro antibacterial activity. Graphical abstract [DISPLAY OMISSION]
유료 다운로드의 경우 해당 사이트의 정책에 따라 신규 회원가입, 로그인, 유료 구매 등이 필요할 수 있습니다. 해당 사이트에서 발생하는 귀하의 모든 정보활동은 NDSL의 서비스 정책과 무관합니다.
원문복사신청을 하시면, 일부 해외 인쇄학술지의 경우 외국학술지지원센터(FRIC)에서
무료 원문복사 서비스를 제공합니다.
NDSL에서는 해당 원문을 복사서비스하고 있습니다. 위의 원문복사신청 또는 장바구니 담기를 통하여 원문복사서비스 이용이 가능합니다.
- 이 논문과 함께 출판된 논문 + 더보기