title: Synthesis and biological evaluation of tricyclic guanidine analogues of batzelladine K for antimalarial, antileishmanial, antibacterial, antifungal and anti-HIV activities.
abstract: Fifty analogues of batzelladine K were synthesized and evaluated for in vitro antimalarial (Plasmodium falciparum), antileishmanial (Leishmania donovani), antimicrobial (panel of bacteria and fungi), antiviral (HIV-1) activities. Analogues 14h and 20l exhibited potential antimalarial activity against chloroquine-sensitive D6 strain with IC501.25 and 0.88 μM and chloroquine-resistant W2 strain with IC501.64 and 1.07 μM, respectively. Analogues 12c and 14c having nonyl substitution showed the most potent antileishmanial activity with IC502.39 and 2.78 μM and IC9011.27 and 12.76 μM respectively. Three analogues 12c, 14c and 14i were the most active against various pathogenic bacteria and fungi with IC50<3.02 μM and MIC/MBC/MFC <6 μM. Analogue 20l having pentyl and methyl substituents on tricycle showed promising activities against all pathogens. However, none was found active against HIV-1. Our study demonstrated that the tricyclic guanidine compounds provide new structral class for broad spectrum activity. © 2012 John Wiley & Sons A/S.
authors.affiliation: Department of Natural Products, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Mohali, Punjab-160062, IndiaNational Center for Natural Products ResearchDepartment of PharmacognosyDepartment of Pharmacology, School of Pharmacy, University of Mississippi, MS 38677, USANational Center for Cell Science (NCCS), Pune University Campus, Ganeshkhind, Pune, Maharashtra-411007, India.
authors.forename: Nafees
authors.initials: N
authors.lastname: Ahmed
authors.affiliation: Department of Natural Products, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Mohali, Punjab-160062, IndiaNational Center for Natural Products ResearchDepartment of PharmacognosyDepartment of Pharmacology, School of Pharmacy, University of Mississippi, MS 38677, USANational Center for Cell Science (NCCS), Pune University Campus, Ganeshkhind, Pune, Maharashtra-411007, India.
authors.forename: Keyur G
authors.initials: KG
authors.lastname: Brahmbhatt
authors.affiliation: Department of Natural Products, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Mohali, Punjab-160062, IndiaNational Center for Natural Products ResearchDepartment of PharmacognosyDepartment of Pharmacology, School of Pharmacy, University of Mississippi, MS 38677, USANational Center for Cell Science (NCCS), Pune University Campus, Ganeshkhind, Pune, Maharashtra-411007, India.
authors.forename: Shabana I
authors.initials: SI
authors.lastname: Khan
authors.affiliation: Department of Natural Products, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Mohali, Punjab-160062, IndiaNational Center for Natural Products ResearchDepartment of PharmacognosyDepartment of Pharmacology, School of Pharmacy, University of Mississippi, MS 38677, USANational Center for Cell Science (NCCS), Pune University Campus, Ganeshkhind, Pune, Maharashtra-411007, India.
authors.forename: Melissa
authors.initials: M
authors.lastname: Jacob
authors.affiliation: Department of Natural Products, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Mohali, Punjab-160062, IndiaNational Center for Natural Products ResearchDepartment of PharmacognosyDepartment of Pharmacology, School of Pharmacy, University of Mississippi, MS 38677, USANational Center for Cell Science (NCCS), Pune University Campus, Ganeshkhind, Pune, Maharashtra-411007, India.
authors.forename: Babu L
authors.initials: BL
authors.lastname: Tekwani
authors.affiliation: Department of Natural Products, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Mohali, Punjab-160062, IndiaNational Center for Natural Products ResearchDepartment of PharmacognosyDepartment of Pharmacology, School of Pharmacy, University of Mississippi, MS 38677, USANational Center for Cell Science (NCCS), Pune University Campus, Ganeshkhind, Pune, Maharashtra-411007, India.
authors.forename: Sudeep
authors.initials: S
authors.lastname: Sabde
authors.affiliation: Department of Natural Products, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Mohali, Punjab-160062, IndiaNational Center for Natural Products ResearchDepartment of PharmacognosyDepartment of Pharmacology, School of Pharmacy, University of Mississippi, MS 38677, USANational Center for Cell Science (NCCS), Pune University Campus, Ganeshkhind, Pune, Maharashtra-411007, India.
authors.forename: Debashis
authors.initials: D
authors.lastname: Mitra
authors.affiliation: Department of Natural Products, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Mohali, Punjab-160062, IndiaNational Center for Natural Products ResearchDepartment of PharmacognosyDepartment of Pharmacology, School of Pharmacy, University of Mississippi, MS 38677, USANational Center for Cell Science (NCCS), Pune University Campus, Ganeshkhind, Pune, Maharashtra-411007, India.
authors.forename: Inder Pal
authors.initials: IP
authors.lastname: Singh
authors.affiliation: Department of Natural Products, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Mohali, Punjab-160062, IndiaNational Center for Natural Products ResearchDepartment of PharmacognosyDepartment of Pharmacology, School of Pharmacy, University of Mississippi, MS 38677, USANational Center for Cell Science (NCCS), Pune University Campus, Ganeshkhind, Pune, Maharashtra-411007, India.
authors.forename: Ikhlas A
authors.initials: IA
authors.lastname: Khan
authors.affiliation: Department of Natural Products, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Mohali, Punjab-160062, IndiaNational Center for Natural Products ResearchDepartment of PharmacognosyDepartment of Pharmacology, School of Pharmacy, University of Mississippi, MS 38677, USANational Center for Cell Science (NCCS), Pune University Campus, Ganeshkhind, Pune, Maharashtra-411007, India.
authors.forename: Kamlesh K
authors.initials: KK
authors.lastname: Bhutani
keywords: Batzelladine; antileishmanial; antimalarial; antimicrobial; anti‐HIV; tricyclic guanidine