1843-35-2

Usage

Uses

Used in Pharmaceutical and Biochemical Research:
3-Azidobenzoic Acid is utilized as a reagent in acylation reactions, which are crucial for the synthesis of various bioactive compounds and pharmaceutical agents. Its azide functionality allows for selective and efficient acylation, facilitating the development of new drugs and therapeutic agents.
Used in Enzyme Studies:
3-Azidobenzoic Acid is employed in studies related to Human UDP-glucuronosyltransferases (UGTs), a family of enzymes that play a significant role in the metabolism and detoxification of endogenous and exogenous compounds. By serving as a substrate or inhibitor in these studies, 3-Azidobenzoic Acid aids in understanding the structure, function, and regulation of UGTs, which is essential for drug development and personalized medicine.

Upstream product

• 99-05-8 meta-aminobenzoic acid 
• 2684-02-8 benzenediazonium 
• 38235-71-1 3-hydrazinobenzoic acid 
• 619-97-6 benzenediazonium nitrate 
• 7782-77-6 cis-nitrous acid 
• 100-63-0 phenylhydrazine 
• 585-76-2 m-bromobenzoic acid 
• 618-51-9 3-Iodobenzoic acid 
• 582-33-2 3-aminobenzoic acid ethyl ester 
• 56423-50-8 3-azido benzoic acid ethyl ester 
• 25116-40-9 3-carboxybenzenediazonium chloride 
• 93066-93-4 methyl 3-azidobenzoate 
• 71-43-2 benzene 

Downstream Products

• 2840-28-0 3-amino-4-chloro-benzoic acid 
• 89-54-3 2-chloro-5-aminobenzoic acid 
• 156266-05-6 C₅₉H₇₈N₄O₁₄Si₂ 
• 259522-68-4 7,10,13-tri(triethylsilyl)-2-debenzoyl-2-(3-azidobenzoyl)-10-deacetylbaccatin III 
• 230283-83-7 2'-O-tert-butyldimethylsilyl-7-O-triethylsilyl-2-debenzoyl-2-(3-azidobenzoyl)-4-deacetyl-4-(methoxycarbonyl)-paclitaxel 
• 330996-87-7 C₅₉H₇₈N₄O₁₃S₂Si₂ 
• 330996-74-2 C₆₁H₈₀N₄O₁₄Si₂ 
• 709633-21-6 C₄₅H₆₉N₃O₁₁Si₂ 
• 709633-25-0 C₄₆H₇₁N₃O₁₁Si₂ 
• 709633-23-8 C₄₈H₆₇N₃O₁₁Si₂ 
• 99-05-8 meta-aminobenzoic acid 
• 1032160-75-0 C₁₆H₂₃N₃O₆ 
• 1098180-70-1 3-azido-N-(6-methylpyridin-2-yl)benzamide 

Relevant academic research and scientific papers

Microwave Assisted Green Synthesis of Pyrazole, 1, 2, 3- Triazole Based Novel Benzohydrazones and Their Antibacterial Activities

A series of novel pyrazole, triazole based benzohydrazones (7a-l) were synthesized via conventional and microwave methods in the presence of acetic acid catalyst. Microwave method provided green and economical approach towards the synthesis of novel Schif

Synthetic approaches, anticancer potential, HSP90 inhibition, multitarget evaluation, molecular modeling and apoptosis mechanistic study of thioquinazolinone skeleton: Promising antibreast cancer agent

New series of compounds bearing 2-thioquinazolinone scaffold were designed, synthesized as HSP90 inhibitors. Anti-proliferative activity of the synthesized compounds was evaluated against HCT-116, Hela and MCF-7 cell lines and compound 5k was found to be

Routes of Synthesis of Carbapenems for Optimizing Both the Inactivation of l, d -Transpeptidase LdtMt1 of Mycobacterium tuberculosis and the Stability toward Hydrolysis by β-Lactamase BlaC

Combinations of β-lactams of the carbapenem class, such as meropenem, with clavulanate, a β-lactamase inhibitor, are being evaluated for the treatment of drug-resistant tuberculosis. However, carbapenems approved for human use have never been optimized for inactivation of the unusual β-lactam targets of Mycobacterium tuberculosis or for escaping to hydrolysis by broad-spectrum β-lactamase BlaC. Here, we report three routes of synthesis for modification of the two side chains carried by the β-lactam and the five-membered rings of the carbapenem core. In particular, we show that the azide-alkyne Huisgen cycloaddition reaction catalyzed by copper(I) is fully compatible with the highly unstable β-lactam ring of carbapenems and that the triazole ring generated by this reaction is well tolerated for inactivation of the l,d-transpeptidase LdtMt1 target. Several of our new carbapenems are superior to meropenem both with respect to the efficiency of in vitro inactivation of LdtMt1 and reduced hydrolysis by BlaC.

Synthesis, characterization, and antimicrobial activity of novel (E)-1-(aryl)-3-{3, 5-dimethoxy-4-[(1-(aryl)-1H-1,2,3-triazol-4-yl)methoxy]phenyl}prop-2-en-1-ones

The new chalcone derivatives containing the 1,2,3-triazole ring system, namely, (E)-1-(aryl)-3-{3,5-dimethoxy-4-[(1-(aryl)-1H-1,2,3-triazol-4-yl)methoxy]phenyl}prop-2-en-1-ones, were synthesized in 65–88% yield by the “click chemistry” reactions of substituted acetophenones, 4-hydroxy-3,5-dimethoxy-benzaldehyde, and different substituted azides. The structure of the compounds was determined by the FT-IR, 1H NMR, 13C NMR, and mass spectroscopic analyses. Compounds 6a–6l were screened for in vitro antimicrobial activity by the agar disc diffusion method.

Benzimidazole–galactosides bind selectively to the Galectin-8 N-Terminal domain: Structure-based design and optimisation

We have obtained the X-ray crystal structure of the galectin-8 N-terminal domain (galectin-8N) with a previously reported quinoline–galactoside ligand at a resolution of 1.6 ?. Based on this X-ray structure, a collection of galactosides derivatised at O3 with triazole, benzimidazole, benzothiazole, and benzoxazole moieties were designed and synthesised. This led to the discovery of a 3-O-(N-methylbenzimidazolylmethyl)–galactoside with a Kd of 1.8 μM for galectin-8N, the most potent selective synthetic galectin-8N ligand to date. Molecular dynamics simulations showed that benzimidazole–galactoside derivatives bind the non-conserved amino acid Gln47, accounting for the higher selectivity for galectin-8N. Galectin-8 is a carbohydrate-binding protein that plays a key role in pathological lymphangiogenesis, modulation of the immune system, and autophagy. Thus, the benzimidazole-derivatised galactosides represent promising compounds for studies of the pathological implications of galectin-8, as well as a starting point for the development of anti-tumour and anti-inflammatory therapeutics targeting galectin-8.

Design, synthesis and molecular docking studies of thymol based 1,2,3-triazole hybrids as thymidylate synthase inhibitors and apoptosis inducers against breast cancer cells

Natural product produced by plants has been the backbone for numerous anticancer agents. In the present work, natural bioactive thymol based 1,2,3-triazole hybrids have been synthesized and evaluated for anticancer activity in MCF-7 and MDA-MB-231 cancer

Naproxen based 1,3,4-oxadiazole derivatives as EGFR inhibitors: Design, synthesis, anticancer, and computational studies

A library of novel naproxen based 1,3,4-oxadiazole derivatives (8–16 and 19–26) has been synthesized and screened for cytotoxicity as EGFR inhibitors. Among the synthesized hy-brids, compound2-(4-((5-((S)-1-(2-methoxynaphthalen-6-yl)ethyl)-1,3,4-oxadiazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)phenol(15) was the most potent compound against MCF-7 and HepG2cancer cells with IC50 of 2.13 and 1.63 μg/mL, respectively, and was equipotent to doxorubicin (IC50 1.62 μg/mL) towards HepG2. Furthermore, compound 15 inhibited EGFR kinase with IC50 0.41 μM compared to standard drug Erlotinib (IC50 0.30 μM). The active compound induces a high percentage of necrosis towards MCF-7, HePG2 and HCT 116 cells. The docking studies, DFT and MEP also supported the biological data. These results demonstrated that these synthesized naproxen hybrids have EGFR inhibition effects and can be used as leads for cancer therapy.

Synthesis and biological evaluation of 1,2,3-triazole tethered thymol-1,3,4-oxadiazole derivatives as anticancer and antimicrobial agents

A library of 1,2,3-triazole-incorporated thymol-1,3,4-oxadiazole derivatives (6–18) hasbeen synthesized and tested for anticancer and antimicrobial activities. Compounds 7, 8, 9, 10, and 11 exhibited significant antiproliferative activity. Among these act

Discovery and structure-activity relationship studies of 1-aryl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as potent dual inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1) and trytophan 2,3-dioxygenase (TDO)

Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO), which mediate kynurenine pathway of tryptophan degradation, have emerged as potential new targets in immunotherapy for treatment of cancer because of their critical role in immunosuppression in the tumor microenvironment. In this investigation, we report the structural optimization and structure-activity relationship studies of 1-phenyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as a new class of IDO1/TDO dual inhibitors. Among all the obtained dual inhibitors, 1-(3-chloro-4-fluorophenyl)-6-fluoro-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione (38) displayed the most potent IDO1 and TDO inhibitory activities with IC50 (half-maximal inhibitory concentration) values of 5 nM for IDO1 and 4 nM for TDO. It turned out that compound 38 was not a PAINS compound. Compound 38 could efficiently inhibit the biofunction of IDO1 and TDO in intact cells. In LL2 (Lewis lung cancer) and Hepa1-6 (hepatic carcinoma) allograft mouse models, this compound also showed considerable in vivo anti-tumor activity and no obvious toxicity was observed. Therefore, 38 could be a good lead compound for cancer immunotherapy and deserving further investigation.

Synthesis and Antimicrobial Activity of Novel Bis-1,2,3-triazol-1H-4-yl-substituted Aryl Benzimidazole-2-thiol Derivatives

Abstract: Novel bis-1,2,3-triazol-1H-4-yl-substitutedaryl benzimidazole-2-thiol derivatives have been synthesized from 5-methoxy and5-difluoromethoxy bis-propargyl substituted benzimidazole-2-thiols using the“click chemistry,” tested for their antimicrobi