16714-23-1

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Uses

Review

Upstream product

• 118-48-9 isatoic anhydride 
• 342-54-1 2-(methoxycarbonyl)benzenediazonium tetrafluoroborate 
• 118-92-3 anthranilic acid 
• 67-56-1 methanol 
• 31162-13-7 2-azidobenzoic acid 
• 552-16-9 ortho-nitrobenzoic acid 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 134-20-3 2-carbomethoxyaniline 
• 606-27-9 methyl 2-nitrobenzoate 
• 34897-85-3 o-azidobenzoyl chloride 

Downstream Products

• 134-20-3 2-carbomethoxyaniline 
• 150205-61-1 3-(methoxycarbonyl)-1,2,4,6-azacycloheptatetraene 
• 115287-27-9 C₂₇H₂₄NO₂P 
• 115255-80-6 C₂₁H₂₀NO₂P 
• 115255-81-7 C₂₂H₂₂NO₂P 
• 940938-75-0 C₁₁H₁₀ClN₃O₂ 
• 1021914-07-7 dimethyl 1-[2-(methoxycarbonyl)phenyl]-1H-1,2,3-triazole-4,5-dicarboxylate 
• 115255-82-8 C₂₃H₂₂NO₂P 

Relevant academic research and scientific papers

Catalyst-Controlled Regioselective Synthesis of Benzotriazlolodiazepin-7-ones and Benzotriazolodiazocin-8-ones

A catalyst-controlled highly chemoselective and regioselective intramolecular cycloamidation of triazol-1-ylbenzamides toward the synthesis of scarcely known heterocycles is reported. In the presence of a palladium catalyst, this cycloisomerization reacti

Cu (I) catalyzed alkyne-azide 1,3-dipolar cycloaddition (CuAAC): Synthesis of 17α-[1-(substituted phenyl)-1,2,3-triazol-4-yl]-19-nor-testosterone-17β-yl acetates targeting progestational and antipro-liferative activities

The progestational potency and selectivity of synthetic steroidal agonists can be enhanced by even larger chemical moieties at 17α-position of the steroid backbones. Hereby a series 5a-c and 6a-c of novel 17α-[1-(substituted phenyl)-1,2,3-triazol-4-yl]-19-nortestosterone-17β-yl acetates were designed and synthesized using click chemistry approach searching progestogenic derivatives with potential anticancer activity. Compounds 5a,b and 6a,c have affected to different extents the three histopatho-logical parameters considered for evaluation of their progestational activity. The compounds 5a,b and 6a,c showed modifications in rat uterus at 35.7-34.8 nM levels with privileged endometrial thickening effect and least change of uterine weight relative to NEA at 52.9 nM level. Up to 40 mg/kg dose compounds 5b and 6c were non-toxic. Molecular docking of the ligands in PR showed in the majority of cases a conformational fitting into the active site different from that of the reference steroid NEA. Compound 6b revealed about 46.4% growth inhibition of CNS cancer SNB-75 cell line, 56% growth inhibition of renal cancer A498 cell line and 56.7% growth inhibition of prostate cancer PC-3 cell line which was mediated by cell cycle arrest. Drugability of the screened compounds showed tolerated results after being challenged to diverse physicochemical parameters.

Rapid synthesis of aryl azides from aryl halides under mild conditions

A rapid synthesis of aryl azides from the corresponding aryl halides catalyzed by CuI/diamine is described. Sodium ascorbate was found to have a positive effect on stabilization of the catalyst system. The reactions were performed under very mild conditions generally with high yields. In the case of aryl iodides, the transformation could be carried out at room temperature. Georg Thieme Verlag Stuttgart.

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.

A general procedure for carbon isotope labeling of linear urea derivatives with carbon dioxide

Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. This article reports on a general approach to label urea derivatives with all carbon isotopes, including14C and11C, based on a Staudinger aza-Wittig sequence. It provides access to all aliphatic/aromatic urea combinations.

Primary discovery of 1-aryl-5-substituted-1H-1,2,3-triazole-4-carboxamides as promising antimicrobial agents

Three series of novel 1H-1,2,3-triazole-4-carboxamides: 1-aryl-5-alkyl/aryl-1H-1,2,3-triazole-4-carboxamides, 1-aryl-5-amino-1H-1,2,3-triazole-4-carboxamides and 1,2,3-triazolo[1,5-a]quinazoline-3-carboxamides were synthesized via base-mediated click azide reactions. Compounds were evaluated for their antimicrobial activities against primary pathogens: Gram-positive and Gram-negative bacterial strains Escherichia coli, Klebsiella pneumonia, Acinetobacter baumannii, Pseudomonas aeruginosa, Staphylococcus aureus, as well as fungal strain Cryptococcus neoformans var. grubii and Candida albicans. Compounds exhibiting moderate to good activities were selected for SAR analysis. Several 5-methyl-1H-1,2,3-triazole-4-carboxamides 4d, 4l, 4r, showed potent antibacterial effect against S. aureus. On the contrary, 5-amino-1H-1,2,3-triazole-4-carboxamide 8b and [1,2,3]triazolo[1,5-a]quinazoline-3-carboxamide 9a were active against pathogenic yeast C. albicans. Thus, compound 4l under 1 μM demonstrated 50% growth inhibition against S. aureus. At the same concentration, the compound 9a killed approx. 40% of C. albicans cells. In general, these compounds demonstrated selective action and no significant impact on the viability of human keratinocytes of HaCaT line.

3-(PHENYLSULFONYL)-[1,2,3]TRIAZOLO[1,5A]QUINAZOLIN-5(4H)-ONE DERIVATIVES

The present invention relates to a compound according to formula (I), wherein R1 and R5 are independently selected from H, halogen, hydroxyl, NO2, CN, C1-C6-alkyl optionally substituted by one or more R11, C1-C6-alkoxy optionally substituted by one or more R11, C3-C6-cycloalkyl optionally substituted by one or more R11, -Cn-alkyl-N(R12)(R13) with n=0-3, -Cn-alkyl-C(O)N(R12)(R13) with n=0-3, -SO2-N(R14)-C(O)-R15; -Cn-alkyl-N(R14)-C(O)-R15 with n=0-3, -Cn-alkyl-C(O)-OR16 with n=0-3, -O(C1-C3-alkyl-O)m-C1-C3-alkyl-OR10 with m=0-3, -Cn-alkyl-OR16 with n=0-3, -NH-Cn-alkyl-R18 with n=0-3; -O-Cn-alkyl-R18 with n=0-3; -OPO(OR10)2, -PO(OR10)2, and a heterocycle optionally substituted by one or more R17; R3 is selected from halogen, hydroxyl, NO2, CN, C1-C6-alkyl optionally substituted by one or more R11, C1-C6-alkoxy optionally substituted by one or more R11, C3-C6-cycloalkyl optionally substituted by one or more R11, -Cn-alkyl-N(R12)(R13) with n=0-3, -Cn-alkyl-C(O)N(R12)(R13) with n=0-3, -SO2-N(R14)-C(O)-R15; -Cn-alkyl-N(R14)-C(O)-R15 with n=0-3, -Cn-alkyl-C(O)-OR16 with n=0-3, -O(C1-C3-alkyl-O)m-C1-C3-alkyl-OR10 with m=0-3, -Cn-alkyl-OR16 with n=0-3, -NH-Cn-alkyl-R18 with n=0-3; -O-Cn-alkyl-R18 with n=0-3; -OPO(OR10)2, -PO(OR10)2, and a heterocycle optionally substituted by one or more R17; R2 and R4 are independently selected from H, halogen, C1-C6-alkyl optionally substituted by one or more R11; R6, R7, R8 and R9 are independently selected from H, halogen, hydroxyl, NO2, CN, C1-C6-alkyl optionally substituted by one or more R11, C1-C6-alkoxy optionally substituted by one or more R11, C3-C6-cycloalkyl optionally substituted by one or more R11, -Cn-alkyl-N(R12)(R13) with n=0-3, -Cn-alkyl-C(O)N(R12)(R13) with n=0-3, -SO2-N(R12)(R13), -SO2-N(R14)-C(O)-R15; -Cn-alkyl-N(R14)-C(O)-R15 with n=0-3, -Cn-alkyl-C(O)-OR16 with n=0-3, -O(C1-C3-alkyl-O)m-C1-C3-alkyl-OR10 with m=0-3, -Cn-alkyl-OR16 with n=0-3, -NH-Cn-alkyl-R18 with n=0-3; -O-Cn-alkyl-R18 with n=0-3; -OPO(OR10)2, -PO(OR10)2, and a heterocycle optionally substituted by one or more R17; R10 is selected from H and C1-C6-alkyl optionally substituted by one or more R11; said one or more R11 is independently selected from Cl, F and hydroxy; R12, R13, R14, R15 and R16 are independently selected from H, C1-C6-alkyl optionally substituted by one or more R11, C3-C6-cycloalkyl optionally substituted by one or more R11, -SO2-C1-C6-alkyl optionally substituted by one or more R11, or wherein said R12 and R13 together with the nitrogen to which they are attached form a heterocycle optionally substituted by one or more R17; said one or more R17 is independently selected from halogen, hydroxy, NO2, CN, -N(R12)(R13), -C(O)-R16, -C(O)-OR16, -Cn-alkyl-OR16 with n=0-3, C1-C6-alkyl optionally substituted by one or more R11, and C1-C6-alkoxy optionally substituted by one or more R11; R18 is selected from -N(R12)(R13), -OR10, -C(O)-R16, -C(O)-OR16, -C(O)- N(R12)(R13), CN, and a heterocycle optionally substituted by one or more R17; and wherein at least one of R1, R2, R4, R5, R6, R7, R8 or R9 is not H; and pharmaceutically acceptable salts, stereoisomers, enantiomers, tautomers of the compounds of formula (I) as well as pharmaceutical compositions thereof and their uses in methods of reducing the virulence of bacteria that express AgrA, in methods for preventing or treating diseases caused or exacerbated by bacteria, preferably by Staphylococcus aureus, such as skin or lung infections or atopic dermatitis.

Optimizing the aryl-triazole of cjoc42 for enhanced gankyrin binding and anti-cancer activity

Gankyrin is an oncoprotein overexpressed in numerous cancer types and appears to play a key role in regulating cell proliferation, cell growth, and cell migration. These roles are largely due to gankyrin's protein-protein interaction with the 26S proteaso

Leucine ureido derivatives as aminopeptidase N inhibitors using click chemistry. Part II

Aminopeptidase N (APN) has been proved to be deeply associated with cancer angiogenesis, metastasis and invasion. Therefore, APN gains increasing attention as a promising anti-tumor target. In the current study, we report the design, synthesis, biological evaluation and structure-activity relationship of one new series of leucine ureido derivatives containing the 1,2,3-triazole moiety. Among them, compound 31f was identified as the best APN inhibitor with IC50 value being two orders of magnitude lower than that of the positive control bestatin. Compound 31f possessed selective cytotoxicity to several tumor cell lines over the normal cell line human umbilical vein endothelial cells (HUVECs). Notably, when combined with 5-fluorouracil (5-Fu), 31f exhibited synergistic anti-proliferation effect against several tumor cell lines. At the same concentration, 31f exhibited much better anti-angiogenesis activities than bestatin in the HUVECs capillary tube formation assay and the rat thoracic aorta rings test. In the in vitro anti-invasion assay, 31f also exhibited superior potency over bestatin. Moreover, considerable in vivo antitumor potencies of 31f alone or in combination with 5-Fu were observed without significant toxic signs in a mouse heptoma H22 tumor transplant model.

Silver(I)-Catalyzed Regioselective Synthesis of Triazole Fused-1,5-Benzoxazocinones

An efficient and regioselective synthesis of novel 1,2,3-triazole-fused-1,5-benzoxazocinones through intramolecular cyclization of substituted ethynyl triazoyl benzoic acids was explored. A crucial precursor 5-iodo-1,2,3-triazole benzoate was obtained fro