Synthesis, XRD, HAS, in silico molecular docking studies and biological assessment of novel Schiff base compounds as anti-cancer and antimicrobial agents

被引：5
作者：
Said, Musa A. [1 ]
Al-Harbi, Wael S. [1 ]
Shanmugam, Mani [1 ,2 ]
Aljohani, Faizah S. [1 ]
Bouqellah, Nahla A. [1 ]
Al-Kaff, Nadia S. [1 ]
机构：
[1] Taibah Univ, Coll Sci, Madinah, Saudi Arabia
[2] IAE, Dept Sci & Humanities, Hyderabad, India
来源：
JOURNAL OF TAIBAH UNIVERSITY FOR SCIENCE | 2020年 / 14卷 / 01期
关键词：
Schiff bases (SB); crystal structure; docking studies; anti-cancer; antimicrobial activity; Enol-imine tautomeric form; Hirshfeld surface analysis; cytotoxicity; CRYSTAL-STRUCTURES; DESIGN; VITRO; CYTOTOXICITY; ANTIOXIDANT; DERIVATIVES; POTENCY; ACID; VIVO; DNA;
D O I：
10.1080/16583655.2020.1849492
中图分类号：
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号：
07 ; 0710 ; 09 ;
摘要：
In this study, versatile multifunctional Schiff base (SB) derivatives were synthesized. Compounds 1-8 were prepared by a mild condition and were pharmacologically assessed for their role in vitro anti-cancer and their impact on human fibrosarcoma (HT-1080) and cervical cancer cells (HeLa), in addition to their antimicrobial activity regarding fungal strains, gram-positive and gram-negative bacteria. Preliminary in silico study of 1-8 and the standard compound (5-Fluorouracil) was accomplished, using Drug2Way and PASS software. Besides, docking investigations were carried out using Schrodinger software to determine the interaction of p53-MDM2 and pf-DHFR binding affinity for all the compounds. The antimicrobial results exhibited that these novel compounds have modest to good inhibitory action against the tried bacterial and fungal strains. The crystal structures of 2 and 7 have been determined. Hirshfeld Surface Analysis (HSA) is in agreement with the XRD studies. Both compounds have shown enol-imine tautomeric forms as EE isomer.
引用
收藏
页码：1590 / 1603
页数：14
相关论文
共 54 条
[21]   Computational structure-activity relationship analysis of non-peptide inducers of macrophage tumor necrosis factor-α production [J].
Khlebnikov, Andrei I. ;
Schepetkin, Igor A. ;
Kirpotina, Liliya N. ;
Quinn, Mark T. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (20) :9302-9312
[22]   Cancer chemotherapy and heterocyclic compounds [J].
Kidwai, M ;
Venkataramanan, R ;
Mohan, R ;
Sapra, P .
CURRENT MEDICINAL CHEMISTRY, 2002, 9 (12) :1209-1228
[23]   Synthesis, antiviral activity and cytotoxicity evaluation of Schiff bases of some 2-phenyl quinazoline-4(3)H-ones [J].
Kumar, Krishnan Suresh ;
Ganguly, Swastika ;
Veerasamy, Ravichandran ;
De Clercq, Erik .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (11) :5474-5479
[24]   Synthesis and in vitro antimalarial activity of tetraoxane-amine/amide conjugates [J].
Kumar, Nitin ;
Khan, Shabana I. ;
Atheaya, Himanshu ;
Mamgain, Ritu ;
Rawat, Diwan S. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (07) :2816-2827
[25]   Computer-Aided Prediction of Rodent Carcinogenicity by PASS and CISOC-PSCT [J].
Lagunin, Alexey ;
Filimonov, Dmitrii ;
Zakharov, Alexey ;
Xie, Wei ;
Huang, Ying ;
Zhu, Fucheng ;
Shen, Tianxiang ;
Yao, Jianhua ;
Poroikov, Vladimir .
QSAR & COMBINATORIAL SCIENCE, 2009, 28 (08) :806-810
[26]   CLC-Pred: A freely available web-service for in silico prediction of human cell line cytotoxicity for drug-like compounds [J].
Lagunin, Alexey A. ;
Dubovskaja, Varvara I. ;
Rudik, Anastasia V. ;
Pogodin, Pavel V. ;
Druzhilovskiy, Dmitry S. ;
Gloriozova, Tatyana A. ;
Filimonov, Dmitry A. ;
Sastry, Narahari G. ;
Poroikov, Vladimir V. .
PLOS ONE, 2018, 13 (01)
[27]   Crystal Structures of Klebsiella pneumoniae Dihydrofolate Reductase Bound to Propargyl-Linked Antifolates Reveal Features for Potency and Selectivity [J].
Lamb, Kristen M. ;
Lombardo, Michael N. ;
Alverson, Jeremy ;
Priestley, Nigel D. ;
Wright, Dennis L. ;
Anderson, Amy C. .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2014, 58 (12) :7484-7491
[28]   Conformationally restricted anti-plasmodial chalcones [J].
Larsen, M ;
Kromann, H ;
Kharazmi, A ;
Nielsen, SF .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (21) :4858-4861
[29]   Expanding the horizon of chemotherapeutic targets: From MDM2 to MDMX (MDM4) [J].
Macchiarulo, Antonio ;
Giacche, Nicola ;
Carotti, Andrea ;
Moretti, Fabiola ;
Pellicciari, Roberto .
MEDCHEMCOMM, 2011, 2 (06) :455-465
[30]  
Macrae CF, 2006, J APPL CRYSTALLOGR, V39, P453, DOI [10.1107/S002188980600731X, 10.1107/S0021 88980600731X]
123456