Dual site reactivity of indole-3-Schiff bases with S/Se/Cl substituted ketenes for stereoselective C-4 substituted indole- β-lactams, biological evaluations, magic chloro effect and molecular docking studies

被引：9
作者：
Sharma, Kiran [1 ,2 ]
Kumar, Pankaj [1 ,2 ]
Sharma, Amita [3 ]
Bari, Shamsher S. [1 ,2 ]
Bhullar, Gaganpreet [4 ]
Sahoo, Subhash C. [1 ,2 ]
Bhalla, Aman [1 ,2 ]
机构：
[1] Panjab Univ, Dept Chem, Chandigarh 160014, India
[2] Panjab Univ, Ctr Adv Studies Chem, Chandigarh 160014, India
[3] Kurukshetra Univ, Dept Bot, Kurukshetra 136119, Haryana, India
[4] Panjab Univ, Dept Microbial Biotechnol, Chandigarh 160014, India
来源：
BIOORGANIC CHEMISTRY | 2024年 / 147卷
关键词：
Indole-beta-lactam; Stereospecific; Molecular hybridization; Antibacterial; Magic chloro effect; ANTIMICROBIAL RESISTANCE;
D O I：
10.1016/j.bioorg.2024.107337
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A convenient methodology for C-4 indole-8-lactam hybrids with chloro, sulphur and seleno substitutions through dual site reactivity of indole-3-Schiff bases towards ketenes has been developed. The reaction proceeded in a stereospecific manner with the exclusive formation of trans-8-lactams assigned with respect to C3-H and C4-H. The synthesized novel 8-lactams have been characterized with the help of elemental analysis (CHNS) and spectroscopic techniques viz. 1H NMR, 13C NMR, DEPT 135, HSQC and IR. The trans configuration was further estabilished based on X-ray crystallographic data. Examination of antibacterial properties unveiled that only derivatives 5a and 5b, featuring chloro substitution, exhibited potent activities, underscoring the emergence of the recently coined term "magic chloro effect". Molecular docking analysis provided additional support for the observed in vitro antibacterial activities of compounds 5a-b.
引用
收藏
页数：9
相关论文
共 38 条
  • [1] Abdellattif M.H., 2021, Front. Chem., P9
  • [2] Alborz M., 2022, ChemistrySelect, P7
  • [3] A brief history of the antibiotic era: lessons learned and challenges for the future
    Aminov, Rustam I.
    [J]. FRONTIERS IN MICROBIOLOGY, 2010, 1
  • [4] Methods for in vitro evaluating antimicrobial activity: A review
    Balouiri, Mounyr
    Sadiki, Moulay
    Koraichi Ibnsouda, Saad
    [J]. JOURNAL OF PHARMACEUTICAL ANALYSIS, 2016, 6 (02) : 71 - 79
  • [5] PROTAC targeted protein degraders: the past is prologue
    Bekes, Miklos
    Langley, David R.
    Crews, Craig M.
    [J]. NATURE REVIEWS DRUG DISCOVERY, 2022, 21 (03) : 181 - 200
  • [6] Structure-activity relationship (SAR) and antibacterial activity of pyrrolidine based hybrids: A review
    Bhat, Aeyaz Ahmad
    Tandon, Nitin
    Singh, Iqubal
    Tandon, Runjhun
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2023, 1283
  • [7] ICF classification of therapeutic goals for outpatient episodes of neurorehabilitation in post-stroke and Parkinson disease
    Bland, Marghuretta D.
    Holleran, Carey L.
    Newman, Caitlin A.
    Fahey, Meghan
    Nordahl, Timothy J.
    DeAngelis, Tamara R.
    Ellis, Teresa D.
    Reisman, Darcy S.
    Earhart, Gammon M.
    Lang, Catherine E.
    [J]. DISABILITY AND REHABILITATION, 2024, 46 (20) : 4772 - 4778
  • [8] IL MILIONE:: a suite of computer programs for crystal structure solution of proteins
    Burla, Maria C.
    Caliandro, Rocco
    Camalli, Mercedes
    Carrozzini, Benedetta
    Cascarano, Giovanni L.
    De Caro, Liberato
    Giacovazzo, Carmelo
    Polidori, Giampiero
    Siliqi, Dritan
    Spagna, Riccardo
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2007, 40 : 609 - 613
  • [9] β-Lactams and β-Lactamase Inhibitors: An Overview
    Bush, Karen
    Bradford, Patricia A.
    [J]. COLD SPRING HARBOR PERSPECTIVES IN MEDICINE, 2016, 6 (08):
  • [10] Cheng Z., 2023, Acta Pharm. Sin. B
1234