N-methyl-4,5-diphenylthiazol-2-amine | 57613-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-methyl-4,5-diphenylthiazol-2-amine
• 英文别名: (4,5-diphenyl-thiazol-2-yl)-methyl-amine；2-Methylamino-4,5-diphenyl-thiazol；2-Methylamino-4,5-diphenylthiazol；2-(Methylamino)-4,5-diphenylthiazole；N-methyl-4,5-diphenyl-1,3-thiazol-2-amine
• CAS: 57613-98-6
• 化学式: C₁₆H₁₄N₂S
• 分子量: 266.367
• InChiKey: GAAGQBXBMOGSPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴苯乙酮 、 N-methyl-4,5-diphenylthiazol-2-amine 以 乙醇 为溶剂， 反应 6.0h， 生成 3-Phenacyl-4.5-diphenyl-thiazolon-(2)-methylimid; 2-Methylimino-4,5-diphenyl-3-phenacyl-thiazolin
  参考文献：
  名称：

  Pyl,T. et al., Justus Liebigs Annalen der Chemie, 1961, vol. 643, p. 145 - 153

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯基乙酮 、 N-甲硫脲 在 cesium bicarbonate 、 三氯溴甲烷 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到N-methyl-4,5-diphenylthiazol-2-amine
  参考文献：
  名称：

  硫脲作为 α-溴化梭合成 5-苯基噻唑胺

  摘要：

  通过硫脲与苯基丙酮、苯基苯乙酮和 β-四氢萘酮的偶联，直接合成了 5-苯基噻唑胺。硫脲作为底物和 α-溴化穿梭，在触发一系列步骤形成最终产物之前，将 Br 从溴化试剂 CBrCl3 转移到羰基部分的 αβ-碳。获得了 80% 至 95% 的分离产率。该协议的主要特点包括最少使用试剂（底物、CBrCl3 和 CsHCO3 作为碱）、温和条件下的反应时间短（80 °C 下 2-3 小时）以及易于放大到克级数量。

  DOI：

  10.1002/ejoc.201601410

文献信息

• General and efficient method for direct N-monomethylation of aromatic primary amines with methanol
  作者：Feng Li、Jianjiang Xie、Haixia Shan、Chunlou Sun、Lin Chen

  DOI：10.1039/c2ra21487c

  日期：——

  The direct N-monomethylation of aromatic primary amines, including arylamines, arylsulfonamides and amino-azoles, using methanol as a methylating agent has been accomplished in the presence of a [Cp*IrCl2]2/NaOH system. From both synthetic and environmental points of view, the reaction is highly attractive because of low catalyst loading, broad substrate scope and excellent selectivities.

  芳族伯胺的直接N-单甲基化反应，包括芳胺，芳基磺酰胺和氨基唑甲醇在[Cp * IrCl 2 ] 2 / NaOH体系的存在下已经完成了甲基化。从合成和环境的角度来看，由于催化剂用量低，底物范围宽和选择性好，该反应具有很高的吸引力。
• NOVEL DIPHENYLTHYAZOLE DERIVATIVE
  申请人：HISAMITSU PHARMACEUTICAL CO. INC.

  公开号：EP0592664A1

  公开（公告）日：1994-04-20

  A novel diphenylthiazole derivative which is effectively used as a medicine with an anti-inflammaory, analgesic, antiallergic, uric acid excretion stimulating, or platelet aggregation inhibiting action and is represented by general formula (I), wherein m and n are each 1 or 2; R¹ and R² each represents hydrogen, lower alkyl, lower alkoxy, lower alkylsulfonyl, nitro, amino, methanesulfonyloxy, or halogen; A¹ represents lower alkanesulfonyl, halogenated lower alkanesulfonyl, substituted bezenesulfonyl, lower acyl, or halogenated lower acyl; and A² represents hydrogen, lower alkanesulfonyl, halogenated lower alkanesulfonyl, or lower alkyl.

  一种新型二苯基噻唑衍生物，可有效用作具有抗炎、镇痛、抗过敏、促进尿酸排泄或抑制血小板聚集作用的药物，由通式(I)表示，其中m和n各为1或2；R¹ 和 R² 各自代表氢、低级烷基、低级烷氧基、低级烷磺酰基、硝基、氨基、甲磺酰氧基或卤素；A¹ 代表低级烷磺酰基、卤代低级烷磺酰基、取代的苯磺酰基、低级酰基或卤代低级酰基；A² 代表氢、低级烷磺酰基、卤代低级烷磺酰基或低级烷基。
• DERIVATIVES OF DIPHENYLTHIAZOLE WITH ANTIINFLAMMATORY ACTIVITY
  申请人：HISAMITSU PHARMACEUTICAL CO. INC.

  公开号：EP0592664B1

  公开（公告）日：2000-07-05
• Microwave promoted synthesis of functionalized 2-aminothiazoles
  作者：George W. Kabalka、Arjun R. Mereddy

  DOI：10.1016/j.tetlet.2006.05.053

  日期：2006.7

  Microwave irradiation promotes the rapid one-pot synthesis of 2-aminothiazoles fromed via the condensation of alpha-bromoketones with thiourea. (c) 2006 Elsevier Ltd. All rights reserved.
• INHIBITION OF CELL PROLIFERATION
  申请人：University of South Florida

  公开号：US20140221658A1

  公开（公告）日：2014-08-07

  The disclosed modulators of Rb:Raf-1 interactions are potent, selective disruptors of Rb:Raf-1 binding, with IC 50 values ranging from 80 nM to 500 nM. Further, these compounds are surprisingly effective in inhibiting a wide variety of cancer cells, including osteosarcoma, epithelial lung carcinoma, non-small cell lung carcinoma, three different pancreatic cancer cell lines, two different glioblastoma cell lines, metastatic breast cancer, melanoma, and prostate cancer. Moreover, the disclosed compounds effectively disrupt angiogenesis and significantly inhibited tumors in nude mice derived from human epithelial lung carcinoma tumors. Accordingly, the disclosed compounds, pharmaceutical compositions comprising the compounds, methods of inhibiting cell proliferation, methods of treating subjects with cancer, and methods of preparing the disclosed compounds are provided.