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primary topic: Synthesis of Bioactive Complex Small Molecule-Ciprofloxacin Conjugates and Evaluation of Their Antibacterial Activity

Synthesis of Bioactive Complex Small Molecule-Ciprofloxacin Conjugates and Evaluation of Their Antibacterial Activity
type: AcademicArticle
type: Article
abstract: Conjugates between pharmaceuticals and small molecules enable access to a vast chemical space required for the discovery of new lead molecules with modified therapeutic potential. However, the dearth of specific chemical reactions that are capable of functionalizing drugs and bioactive natural products presents a formidable challenge for preparing their conjugates. Here, we report a support-free CuI-nanoparticle-catalyzed strategy for conjugating electron-deficient and electron-rich terminal alkynes with a ciprofloxacin methyl ester. Our conjugation technique exploits the late-stage functionalization of bioactive natural products such as tocopherol, vasicinone, amino acids, and pharmaceuticals such as aspirin and paracetamol to provide conjugates in excellent yields under mild and green conditions. This protocol also enabled the synthesis of (hetero)arene-ciprofloxacin 1,4-disubstituted 1,2,3-triazoles in good yields and high regioselectivities. These synthesized ciprofloxacin conjugates were evaluated in vitro for their antibacterial activity against a panel of relevant bacteria. A significant number of conjugates showed comparable activity against Gram-positive and Gram-negative bacteria. Moreover, some conjugates exhibited less toxicity than ciprofloxacin against two mammalian cell lines, suggesting the utility for the future investigation of these compounds for in vivo efficacy and pharmacokinetic studies.
date: 2020-07-21
volume: 22
issue: 9
status: peerReviewed
status: published
author list: authors
type: EPrint
type: ArticleEPrint
is part of: repository
subject: QR Microbiology

American Chemical Society
type: Organization

ACS Combinatorial Science
type: Collection

Onkar S Nayal
type: Person
given name: Onkar S
family name: Nayal

Rohit Rana
type: Person
given name: Rohit
family name: Rana

Sushil K Maurya
type: Person
given name: Sushil K
family name: Maurya

Hemraj Nandanwar
type: Person
given name: Hemraj
family name: Nandanwar

Manoj Jangra
type: Person
given name: Manoj
family name: Jangra

Rahul Kumar
type: Person
given name: Rahul
family name: Kumar

Rahul Upadhyay
type: Person
given name: Rahul
family name: Upadhyay

HTML Summary of #2592 Synthesis of Bioactive Complex Small Molecule-Ciprofloxacin Conjugates and Evaluation of Their Antibacterial Activity
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primary topic: Synthesis of Bioactive Complex Small Molecule-Ciprofloxacin Conjugates and Evaluation of Their Antibacterial Activity

QR Microbiology
type: Concept