N-(4-(2-氨基噻唑-4-基)苯基)苯甲酰胺 | 299441-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-(2-氨基噻唑-4-基)苯基)苯甲酰胺
• 英文名称: N-(4-(2-aminothiazol-4-yl)phenyl)benzamide
• 英文别名: N-[4-(2-amino-1,3-thiazol-4-yl)phenyl]benzamide
• CAS: 299441-52-4
• 化学式: C₁₆H₁₃N₃OS
• mdl: MFCD01119367
• 分子量: 295.365
• InChiKey: WNMRWBLANCRRGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-二甲基-1,3-噻唑-5-羧酸 、 N-(4-(2-氨基噻唑-4-基)苯基)苯甲酰胺 在 吡啶 、 propylphosphonic anhydride 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 96.0h， 以48%的产率得到N-(4-(4-benzamidophenyl)thiazol-2-yl)-2,4-dimethylthiazole-5-carboxamide
  参考文献：
  名称：

  COMPOSITIONS AND METHODS OF TARGETING MUTANT K-RAS

  摘要：

  提供了抑制K-ras，尤其是突变K-ras的化合物和组合物。某些化合物优先或甚至选择性地抑制特定形式的突变K-Ras，特别是G12D突变形式。

  公开号：

  US20180086752A1
• 作为产物：
  描述：

  N-苯甲酰替苯胺 在 二硫化碳 、 aluminum (III) chloride 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 N-(4-(2-氨基噻唑-4-基)苯基)苯甲酰胺
  参考文献：
  名称：

  COMPOSITIONS AND METHODS OF TARGETING MUTANT K-RAS

  摘要：

  提供了抑制K-ras，尤其是突变K-ras的化合物和组合物。某些化合物优先或甚至选择性地抑制特定形式的突变K-Ras，特别是G12D突变形式。

  公开号：

  US20180086752A1

文献信息

• Synthesis and biological evaluation of anti-tubercular activity of Schiff bases of 2-Amino thiazoles
  作者：Rachel Cordeiro、Monica Kachroo

  DOI：10.1016/j.bmcl.2020.127655

  日期：2020.12

  2-[4-(2-Amino-thiazol-4-yl)-phenyl]-isoindole-1,3-dione derivatives with 3,4,5-trimethoxy substitution (5b1) and the compound 1-[4-(2-Amino-thiazol-4-yl)-phenyl]-pyrrole-2,5-dione (4a) which is a maleic derivative bearing thiazole ring, exhibited good anti-tubercular activity (MIC 6.25 μg/ml). Drug likeness was also evaluated for all the synthesised compounds using Molinspiration software. All synthesized

  据报告，结核病是一种传染性疾病，2018年将导致150万人死亡。由于多药耐药结核病，广泛耐药结核病和完全耐药结核病的出现，许多是一线和二线的已发现在线药物无效。结核病治疗方案中引入的新药，如前驱体前药，苯达喹啉和利奈唑胺已与毒性相关。因此，迫切需要引入安全且具有成本效益的抗结核药物。在这项研究中，合成了一系列2-氨基噻唑的席夫碱，并通过微孔板阿拉法蓝测定法（MABA）评估了它们对结核分枝杆菌H37Rv菌株的抗结核活性。N- [4-（2-氨基-噻唑-4-基）-苯基]-苯甲酰胺衍生物与2-硝基（5c 2），4-羟基（5c 4）取代，2- [4-（2-氨基-噻唑-4-基）-苯基]-异吲哚-1,3-二酮衍生物，3,4,5-三甲氧基取代（5b 1）和具有噻唑环的马来酸衍生物的化合物[1- [4-（2-氨基-噻唑-4-基）-苯基]-吡咯-2，5-二酮（4a）显示出良好的抗结核活性。 （MIC 6.25μg/
• Synthesis of a Thiazole Library via an Iridium-Catalyzed Sulfur Ylide Insertion Reaction
  作者：Storm Hassell-Hart、Elisa Speranzini、Sirihathai Srikwanjai、Euan Hossack、S. Mark Roe、Daren Fearon、Daniel Akinbosede、Stephen Hare、John Spencer

  DOI：10.1021/acs.orglett.2c02996

  日期：2022.11.4

  A library of thiazoles and selenothiazoles were synthesized via Ir-catalyzed ylide insertion chemistry. This process is a functional group, particularly heterocycle-substituent tolerant. This was applied to the synthesis of fanetizole, an anti-inflammatory drug, and a thiazole-containing drug fragment that binds to the peptidyl-tRNA hydrolase (Pth) in Neisseria gonorrheae bacteria.

  通过 Ir 催化叶立德插入化学合成了噻唑和硒代噻唑库。这个过程是一个官能团，特别是杂环取代基的耐受性。该技术被应用于合成抗炎药法奈替唑以及与淋病奈瑟菌细菌中的肽基-tRNA水解酶（Pth）结合的含噻唑药物片段。
• Design, synthesis and in vitro antimicrobial activity of novel phenylbenzamido-aminothiazole-based azasterol mimics
  作者：Rama Krishna Yadlapalli、O. P. Chourasia、Madhu Prakash Jogi、Appa Rao Podile、Ramu Sridhar Perali

  DOI：10.1007/s00044-012-0314-5

  日期：2013.6

  Phenylbenzamide framework as a mimic of the azasterol structure was investigated by synthesizing 4-phenylbenzamido-2-aminothiazole 4, and evaluating its MIC against Escherichia coli, Enterobacter cloacae, Bacillus licheniformis and Mycobacterium tuberculosis (MTB) H(37)Rv as well as antifungal activity against three test phytopathogenic fungi. Further, the bioisosterism strategy was implemented to synthesize a series of azo-derivatives of 4 (6a-6j). All the azo-compounds were screened for their antibacterial and antifungal activity. The electronic (UV-vis) absorption characteristics of the final compounds were examined. Resazurin-mediated microtitre plate-antibacterial assay was implemented for first time on these azo-derivatives. Compounds 4 and 6b had significant antibacterial activity. For the compound 4, MIC against Escherichia coli is 7.8 x 10(-3) mg/mL and MIC against Mycobacterium tuberculosis (MTB) H(37)Rv is 16 mu g/mL were identified. Compounds 4, 6d, 6g and 6h showed excellent antifungal activity, when compared to the standard nistatin, against three test phytopathogenic fungi.
• [EN] COMPOSITIONS AND METHODS OF TARGETING MUTANT K-RAS<br/>[FR] COMPOSITIONS ET MÉTHODES DE CIBLAGE DE K-RAS MUTANT
  申请人：NANTBIOSCIENCE INC

  公开号：WO2016161361A1

  公开（公告）日：2016-10-06

  Compounds and compositions are presented that inhibit K-ras, and especially mutant K-ras. Certain compounds preferentially or even selectively inhibit specific forms of mutant K-Ras, and particularly the G12D mutant form.