Tail approach synthesis of novel benzenesulfonamides incorporating 1,3,4-oxadiazole hybrids as potent inhibitor of carbonic anhydrase I, II, IX, and XII isoenzymes.

08:00 EDT 10th March 2020 | BioPortfolio

Summary of "Tail approach synthesis of novel benzenesulfonamides incorporating 1,3,4-oxadiazole hybrids as potent inhibitor of carbonic anhydrase I, II, IX, and XII isoenzymes."

Two new series of 1,3,4-oxadiazole benzenesulfonamide hybrids 3 and 4, having twenty novel compounds, have been designed and synthesized in order to assess their inhibition potential as CAIs against hCA I, II, IX, and XII. 'Tail approach' strategy has been used to design the aromatic sulfonamide scaffolds with carbonyl and amide linker. Excellent inhibitory activity against hCA I has been exhibited by compounds 3g and 4j, 3.5 magnitude of order better than reference drug AAZ (K = 250 nM). Moreover, compound 4j (K = 7.9 nM) effectively inhibited glaucoma-associated hCA II isoform as well as tumor-associated hCA IX isoform with K = 16.3 nM. Further hCA XII was weakly inhibited by all the compounds with K values ranging from 0.23 μM to 3.62 μM. Interestingly structure-activity relationship (SAR) study indicates that N-(3-nitrophenyl)-2-((5-(4-sulfamoylphenyl)-1,3,4-oxadiazol-2-yl)thio)acetamide (4j) is a potent compound to be investigated further for antiglaucoma and antitumor activity. The chemistry of the nature of different substitutions on the 1,3,4-oxadiazole bearing benzenesulfonamide substituted aromatic ring for potency and selectivity over one hCA isoform versus others is deliberated in the present study. In this context, the 1,3,4-oxadiazole motif can be a valuable tool worth developing for the procurement of novel and potent selective CAIs potentially useful for the management of a variety of diseases as chemotherapeutic agents.


Journal Details

This article was published in the following journal.

Name: European journal of medicinal chemistry
ISSN: 1768-3254
Pages: 112219


DeepDyve research library

PubMed Articles [11484 Associated PubMed Articles listed on BioPortfolio]

Continued exploration and tail approach synthesis of benzenesulfonamides containing triazole and dual triazole moieties as carbonic anhydrase I, II, IV and IX inhibitors.

A library of twenty two novel 1,2,3-triazole benzenesulfonamides incorporating thiosemicarbazide, 5(4H)-thione-1,2,4-triazole and variously substituted phenacyl appended 1,2,4-triazole as tail were de...

Synthesis and structure-affinity relationship of chlorinated pyrrolidinone-bearing benzenesulfonamides as human carbonic anhydrase inhibitors.

A novel set of pyrrolidinone-based chlorinated benzenesulfonamide derivatives were synthesized and investigated for their binding affinity and selectivity against recombinant human carbonic anhydrases...

Design, synthesis, and biological evaluation of ferulic acid based 1,3,4-oxadiazole hybrids as multifunctional therapeutics for the treatment of Alzheimer's disease.

Thirty ferulic acid-based 1,3,4-oxadiazole molecular hybrids were designed, synthesized, and screened them for multifunctional inhibitory potential against acetylcholinesterase (AChE), butyrylcholines...

Association of Insect-Derived Ear Injury With Yield and Aflatoxin of Maize Hybrids Varying in Bt Transgenes.

Environmental factors have been associated with the production of aflatoxin in maize, Zea mays L., and it is inconclusive whether transgenic, Bacillus thuringiensis (Bt), maize has an impact on aflato...

Chloride-Assisted Peptide Macrocyclization.

The role of the Cl anion as a templating agent for the synthesis of cyclopeptides was assessed through the preparation of three new homocyclolysines and other six cyclic peptides by head-to-tail lacta...

Clinical Trials [2727 Associated Clinical Trials listed on BioPortfolio]

Laparoscopic vs Open Pancreatectomy for Body and Tail Pancreatic Cancer

Open distal pancreatectomy (ODP) has been commonly employed for the treatment of a variety of cancers in body and tail of pancreas. Although many general surgical procedures have been incr...

A Study Evaluating the Effects of Lipid Lowering Treatment on Steroid Synthesis

Cholesterol is the precursor of glucocorticoids, mineralocorticoids and sex steroids. Both adrenal and non-adrenal (ovarian + testicular) all steroid hormones are primarily synthesized usi...

RAMPS VS SRPS for Pancreatic Body and Tail Adenocarcinoma

Two arms RCT is design, patients with pancreatic body or tail adenocarcinoma will be randomly assigned to the Radical Antegrade Modular Pancreaticosplenectomy (RAMPS) group or Standard Ret...

Effects of Oral Supplementation of Arginine, Zinc and Vitamin C on Collagen Synthesis in Inguinal Hernia Patients

Collagen synthesis is depressed systemically in the immediate postoperative period. Arginine, zinc and vitamin C impact collagen synthesis. The aim of this study is to investigate the eff...

Randomized Study Assessing the Effect of Transpapillary Pancreas Duct Stent in Resection of the Pancreatic Tail

Randomized study assessing the effect of transpapillary pancreas duct stent in resection of the pancreatic tail.

Medical and Biotech [MESH] Definitions

RNA sequences that serve as templates for protein synthesis. Bacterial mRNAs are generally primary transcripts in that they do not require post-transcriptional processing. Eukaryotic mRNA is synthesized in the nucleus and must be exported to the cytoplasm for translation. Most eukaryotic mRNAs have a sequence of polyadenylic acid at the 3' end, referred to as the poly(A) tail. The function of this tail is not known for certain, but it may play a role in the export of mature mRNA from the nucleus as well as in helping stabilize some mRNA molecules by retarding their degradation in the cytoplasm.

A nitrovinyl furan used as a schistosomicidal agent and proposed for trypanosomiasis, especially Chagas disease.

Proteins found in the tail sections of DNA and RNA viruses. It is believed that these proteins play a role in directing chain folding and assembly of polypeptide chains.

Any situation where an animal or human is trained to respond differentially to two stimuli (e.g., approach and avoidance) under reward and punishment conditions and subsequently trained under reversed reward values (i.e., the approach which was previously rewarded is punished and vice versa).

The family Erinaceidae, in the order INSECTIVORA. Most are true hedgehogs possessing a coat of spines and a very short tail. Those members of the family found in Southeast Asia (moonrats or gymnures) have normal body hair and a long tail.

Quick Search

DeepDyve research library

Relevant Topic

Drug Discovery
Clinical Approvals Clinical Trials Drug Approvals Drug Delivery Drug Discovery Generics Drugs Prescription Drugs In the fields of medicine, biotechnology and pharmacology, drug discovery is the process by which drugs are dis...

Searches Linking to this Article