99519-84-3

Usage

Uses

Used in Pharmaceutical Industry:
5-Amino-1-(3,5-dichloro-4-(4-chlorobenzoyl)benzyl)-1H-1,2,3-triazole-4-carboxamide is used as an orally active calcium channel blocker for the treatment of various cardiovascular conditions. Its ability to block calcium channels helps in regulating blood flow and reducing blood pressure, making it a potential candidate for hypertension and other related disorders.
Used in Anti-cancer Applications:
In the field of oncology, Carboxyamidotriazole exhibits potential anti-cancer properties by inhibiting the production of pro-inflammatory cytokines in tumor-associated macrophages. This mechanism may help in reducing inflammation and limiting the growth and progression of cancer cells, offering a novel therapeutic approach for cancer treatment.
Used in Drug Discovery and Development:
Due to its unique chemical structure and biological activities, 5-Amino-1-(3,5-dichloro-4-(4-chlorobenzoyl)benzyl)-1H-1,2,3-triazole-4-carboxamide can be further explored and optimized for drug discovery and development. Its potential as a calcium channel blocker and anti-inflammatory agent makes it a promising candidate for the development of new drugs targeting cardiovascular and oncological diseases.

Biological Activity

Orally active Ca 2+ channel blocker; inhibits K + - and carbachol-stimulated Ca 2+ influx (IC 50 values are 500 and 935 nM respectively). Exhibits antiproliferative, antiangiogenic and antimetastatic activity in vivo and displays selectivity towards numerous mismatch repair-deficient tumor cell lines in vitro .

InChI:InChI=1/C17H12Cl3N5O2/c18-10-3-1-9(2-4-10)15(26)13-11(19)5-8(6-12(13)20)7-25-16(21)14(17(22)27)23-24-25/h1-6H,7,21H2,(H2,22,27)

Upstream product

• 25186-47-4 3,5-dichlorotoluene 
• 99520-09-9 (4-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-dichlorophenyl)(4-chlorophenyl)methanone 
• 60211-57-6 3,5-dichlorobenzyl alcohol 
• 99508-25-5 (4-chlorophenyl)(2,6-dichloro-4-(hydroxymethyl)phenyl)methanone 
• 99508-26-6 (4-(azidomethyl)-2,6-dichlorophenyl)(4-chlorophenyl)methanone 
• 99508-24-4 (4-(bromomethyl)-2,6-dichlorophenyl)(4'-chlorophenyl)methanone 
• 99508-23-3 2',6',4''-trichloro-4'-methylbenzophenone 
• 99508-22-2 2,6-dichloro-4-methylbenzoyl chloride 
• 99520-05-5 2,6-dichloro-4-methylbenzoic acid 
• 122-01-0 4-chloro-benzoyl chloride 
• 107-91-5 cyanoacetic acid amide 

Downstream Products

• 187739-60-2 5-amino-1-(4-[4-chlorobenzoyl]-3,5-dichlorobenzyl)-1,2,3-triazole-4 carboxamide orotate 
• 154087-05-5 5-benzamido-1-(3,5-dichloro-4-(4-chlorobenzoyl)benzyl)-1H-1,2,3-triazole-4-carboxamide 

Relevant academic research and scientific papers

Method for synthesizing carboxamide triazole

The invention relates to a method for synthesizing carboxamide triazole. The method for synthesizing carboxamide triazole comprises the following steps: (1) sequentially carrying out halogenation reaction and azide substitution reaction by adopting a one-

Identification of a novel toxicophore in anti-cancer chemotherapeutics that targets mitochondrial respiratory complex i

Disruption of mitochondrial function selectively targets tumour cells that are dependent on oxidative phosphorylation. However, due to their high energy demands, cardiac cells are disproportionately targeted by mitochondrial toxins resulting in a loss of cardiac function. An analysis of the effects of mubritinib on cardiac cells showed that this drug did not inhibit HER2 as reported, but directly inhibits mitochondrial respiratory complex I, reducing cardiac-cell beat rate, with prolonged exposure resulting in cell death. We used a library of chemical variants of mubritinib and showed that modifying the 1H-1,2,3-triazole altered complex I inhibition, identifying the heterocyclic 1,3-nitrogen motif as the toxicophore. The same toxicophore is present in a second anti-cancer therapeutic carboxyamidotriazole (CAI) and we demonstrate that CAI also functions through complex I inhibition, mediated by the toxicophore. Complex I inhibition is directly linked to anti-cancer cell activity, with toxicophore modification ablating the desired effects of these compounds on cancer cell proliferation and apoptosis.

Preparation of Solid Polyfunctional Alkynylzinc Pivalates with Enhanced Air and Moisture Stability for Organic Synthesis

We report the preparation of solid and air-stable polyfunctionalized alkynylzinc pivalates from the corresponding alkynes using TMPZnOPiv (TMP=2,2,6,6-tetramethylpiperidyl) as base. These organozinc pivalates are obtained as powders under mild conditions

Novel compositions and processes for preparing 5-amino or substituted amino 1,2,3-triazoles and triazoles orotate formulations

New polymorphs of 5-amino or substituted amino 1,2,3-triazole and substituted derivatives thereof, of orotates of the carboxyamidotriazoles, of formulations of the triazoles and orotic acid in the ratio of 1:1 to 1:4 (base:acid) and of safer processes of

NOVEL COMPOSITIONS AND PROCESSES FOR PREPARING 5-AMINO OR SUBSTITUTED AMINO 1,2,3-TRIAZOLES AND TRIAZOLE OROTATE FORMULATIONS

New polymorphs of 5-amino or substituted amino 1, 2, 3-triazole and substituted derivatives thereof, of orotates of the carboxyamidotriazoles, of formulations of the triazoles and orotic acid in the ratio of 1:1 to 1:4 (base:acid) and of safer processes o

Benzylated 1,2,3-triazoles as anticoccidiostats

Substituted 5-amino-4-carbamoyl-1,2,3-triazoles 3a-w were prepared by two synthetic schemes and evaluated in vivo for anticoccidial activity. Both schemes proceeded by brominating appropriately substituted toluenes 4a-s,v to 5a-s,v. In Scheme I, the brominated benzyl analogues 5 were converted to the corresponding benzyl azides 6, which were treated with cyanoacetamide to yield 1-substituted-5-amino-4-carbamoyl-1,2,3-triazoles 3. In Scheme II, the benzyl halides 5 were employed to alkylate the sodium salt of 5-amino-4-carbamoyl-1,2,3-triazole (7). Preliminary screening data against Eimeria acervulina and E. tenella in chickens suggested structural requirements for maximizing activity. Further evaluation against a relatively resistant series of eight Eimeria field isolates revealed L-651,582 (3a) to be a highly effective coccidiostat. However, unacceptable tissue residues precluded further development. Mechanistic studies on this series of 5-amino-4-carbamoyl-1,2,3-triazoles and, in particular, on L-651,582 (3a) revealed that its mode of action does not involve inhibition of IMP dehydrogenase, but probably interferes with host cell calcium entry. In addition, L-651,582 has been found to have antiproliferative activity in several disease models and was recently reported to possess antimetastatic activity in a model of ovarian cancer progression.

An Improved Procedure for the Preparation of 1-Benzyl-1H-1,2,3-triazoles from Benzyl Azides.

A procedure for the preparation of substituted 1-benzyl-1H-1,2,3-triazoles from benzyl azides under very mild conditions is described.The method provides improved yields and extends the scope of the Dimroth Reaction to other types of active methylene compound to those previously used.Benzyl azides react with active methylene compounds in dimethyl sulphoxide catalysed by potassium carbonate at 35-40 deg C to give 1H-1,2,3-triazoles usually in good yield.Acetonitrile derivatives gave 5-amino-1H-1,2,3-triazoles whereas diethyl malonate gave 5-hydroxy-1H-1,2,3-triazoles. 1H-1,2,3-Triazole-4-carboxylate esters and 1H-1,2,3-triazole-4-ketones were obtained from ethyl acetoacetate and β-diketones respectively.Benzyl methyl ketone reacted to give 5-methyl-4-phenyl-1H-1,2,3-triazole, but acetone and acetophenone failed to react.Other active methylene compounds which did not react under these reaction conditions included ethyl cyanoacetate, ethyl fluoroacetate and ethyl nitroacetate.

5-amino or substituted amino 1,2,3-triazoles

Novel 5-amino or substituted amino 1,2,3-triazoles are disclosed as having anticoccidial activity. The compounds are useful for controlling coccidiosis when administered in minor quantities to animals, in particular to poultry, usually in admixture with a