5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbonyl chloride | 88958-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbonyl chloride
• 英文别名: 5-methyl-1-(4-methylphenyl)triazole-4-carbonyl chloride
• CAS: 88958-20-7
• 化学式: C₁₁H₁₀ClN₃O
• 分子量: 235.673
• InChiKey: JADFIFDJQGJGRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbonyl chloride 在 四磷十氧化物 、 potassium carbonate 、 三氯氧磷 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 24.0h， 生成 1-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]-6-chloro-4,9-dihydro-3H-β-carboline
  参考文献：
  名称：

  Synthesis of 1-(1-aryl-1H-1,2,3-triazol-4-yl)-β-carboline derivatives

  摘要：

  Reaction of 5-methyl-1-aryl-1H-1,2,3-triazole-4-carbocylic acid chlorides with tryptamine derivatives afforded substituted 1-aryl-N-[2-(1H-indol-3-yl)ethyl]-5-methyl-1H-1,2,3-triazole-4-carboxamides. At heating these compounds in toluene in the presence of POCl3 and P2O5 Bischler-Napieralski cyclization occurs giving 1-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-4,9-dihydro-3H-beta-carbolines that can be transformed into beta-carboline and tetrahydro-beta-carboline derivatives.

  DOI：

  10.1134/s1070428014020225
• 作为产物：
  描述：

  p-叠氮甲苯 在 氯化亚砜 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbonyl chloride
  参考文献：
  名称：

  某些新的（S）-1-芳基-N-（1-羟基-3-苯基丙烷-2-基）-5-甲基-1H-1,1,2,3-三唑-4-羧酰胺的合成

  摘要：

  一些新的（S）-1-芳基-N-（1-羟基-3-苯基丙烷-2-基）-5-甲基-1  H -1,2,3-三唑-4羧酰胺4a，4b，4c，已通过1 H和13合成并建立了4d，4e，4f，4g，4h，4i，4jC NMR，IR，MS光谱，CHN分析和X射线衍射晶体学。分子间H键O2'-H2'··O1，O2‐H2···O1'和分子内H键N4'-H4'N··N3'，N4的相互作用稳定了分子构象和堆积'-H4'N···O2'，N4-H4N···N3，N4-H4N···O2。五个数字的两个环是通过分子中的H键形成的。

  DOI：

  10.1002/jhet.1567

文献信息

• Synthesis of 1<i>H-</i>1,2,3-triazole-4-carbonitriles as building blocks for promising 2-(triazol-4-yl)-thieno[2,3-d]pyrimidine drug candidates
  作者：Taras V. Sekh、Olga Y. Shyyka、Nazariy T. Pokhodylo、Mykola D. Obushak

  DOI：10.1080/00397911.2021.1966041

  日期：2021.10.18

  Abstract A new synthetic route leading to functionalized 1H-1,2,3-triazole-4-carbonitriles has been developed. A set of 1-aryl-5-methyl-1H-1,2,3-triazole-4-carbonitriles was obtained in high yields from readily available starting 1H-1,2,3-triazole-4-carboxylic acids via several synthetic protocols. Synthesized 1H-1,2,3-triazole-4-carbonitriles were examined as promising precursors in the simple and efficient

  摘要 已经开发了导致功能化的 1 H -1,2,3-三唑-4-腈的新合成路线。一组 1-芳基-5-甲基-1 H -1,2,3-三唑-4-甲腈从容易获得的起始 1 H -1,2,3-三唑-4-羧酸中以高收率获得几种合成方案。合成的 1 H -1,2,3-三唑-4-腈被认为是一种简单有效的制备 2-三唑-4-基-噻吩并[2,3- d ]嘧啶的有前途的前体。这种方法允许创建用于抗癌药物发现的广泛组合库。
• 10.1016/j.molstruc.2024.138743
  作者：Pokhodylo, Nazariy、Тupychak, Mykola、Finiuk, Nataliya、Klyuchivska, Olha、Stoika, Rostyslav

  DOI：10.1016/j.molstruc.2024.138743

  日期：——

  pharmacophore hybridization strategy to combine biologically active scaffolds was implemented for design and synthesis of benzoisothiazole-1,2,3-triazole-4-carboxamide conjugates via piperazine linker. screening led to identification of the compounds and , with para-chlorine- or fluorine- substitution on the phenyl ring, and isopropyl or cyclopropyl substituents in position 5 of 1,2,3-triazole cycle

  采用结合生物活性支架的药效团杂交策略，通过哌嗪接头设计和合成苯并异噻唑-1,2,3-三唑-4-甲酰胺缀合物。筛选结果鉴定出化合物 和 ，其苯环上有对位氯或氟取代，并且 1,2,3-三唑环的 5 位有异丙基或环丙基取代基，是有效的抗癌剂。这些化合物在亚微摩尔浓度下对 MCF-7 系人乳腺癌细胞具有毒性，IC50 分别为 0.76 ± 0.04 μM 和 0.90 ± 0.02 μM，而对正常细胞没有毒性 (IC50 > 100 μM)。衍生物和 能有效抑制癌MCF-7细胞的集落形成和增殖。这些衍生物导致 MCF-7 细胞 DNA 断裂。我们认为这些化合物的 DNA 损伤作用可能与它们插入 DNA 分子的高能力有关，这种能力与已知的抗癌剂阿霉素的能力相当。使用计算分子对接证实了化合物和 DNA 的高亲和力。
• Primary discovery of 1-aryl-5-substituted-1H-1,2,3-triazole-4-carboxamides as promising antimicrobial agents
  作者：Nazariy Pokhodylo、Nazar Manko、Nataliya Finiuk、Olha Klyuchivska、Vasyl Matiychuk、Mykola Obushak、Rostyslav Stoika

  DOI：10.1016/j.molstruc.2021.131146

  日期：2021.12
• Synthesis and anticancer activity evaluation of new 1,2,3-triazole-4-carboxamide derivatives
  作者：Nazariy Pokhodylo、Olga Shyyka、Vasyl Matiychuk

  DOI：10.1007/s00044-013-0841-8

  日期：2014.5

  Anticancer screening of several novel 1,2,3-triazoles has been performed. The 1,2,3-triazole derivatives were synthesized from available starting materials according to the convenient synthetic procedures using a multicomponent reaction which gave a wide access to triazole derivatives production. The synthesized compounds were tested for their anticancer activity in NCI60 cell lines. It was observed that some compounds showed remarkable anticancer activity. Two of them possessed a significant activity on leukemia, melanoma, non-small cell lung, CNS, ovarian, renal, and breast cancer. 5-Amino-1-p-tolyl-1H-[1,2,3]triazole-4-carboxylic acid (2,5-dichloro-phenyl)-amide showed a significant correlation in COMPARE analysis.1,2,3-triazole-4-carboxamide derivatives were synthesized in a simple and convenient synthetic path, their in vitro anticancer activity was examined after the performance of molecular docking.
• Synthesis of 1,2,4- and 1,3,4-oxadiazoles from 1-aryl-5-methyl-1H-1,2,3-triazole-4-carbonyl chlorides
  作者：N. D. Obushak、N. T. Pokhodylo、N. I. Pidlypnyi、V. S. Matiichuk

  DOI：10.1134/s1070428008100217

  日期：2008.10

  5-Substituted 2-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazoles were synthesized by reaction of 1-aryl-5-methyl-1H-1,2,3-triazole-4-carbonyl chlorides with the corresponding 5-substituted 1H-tetrazoles. 5-Methyl-1-phenyl-1H-1,2,3-triazole-4-carbonyl chloride reacted with N'-hydroxybenzimidamides to give 3-aryl-5-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazoles. Reactions of 4-(5-methyl-1H-1,2,3-triazol-1-yl)benzoic acid with N'-hydroxybenzimidamides resulted in the formation of 3-aryl-5-[4-(5-methyl-1H-1,2,3-triazol-1-yl)phenyl]-1,2,4-oxadiazoles.