4-chloro-N-phenyl[1,3]thiazolo[4,5-d][1,2,3]triazine-6-amine | 1069114-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloro-N-phenyl[1,3]thiazolo[4,5-d][1,2,3]triazine-6-amine
• 英文别名: 4‐chlorothiazolotriazine；4-chloro-N-phenyl-[1,3]thiazolo[4,5-d]triazin-6-amine
• CAS: 1069114-94-8
• 化学式: C₁₀H₆ClN₅S
• 分子量: 263.71
• InChiKey: XVIUHUVUSKJAIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  吗啉 、 4-chloro-N-phenyl[1,3]thiazolo[4,5-d][1,2,3]triazine-6-amine 反应 6.0h， 以76%的产率得到4-(4-morpholinyl)-N-phenyl[1,3]thiazolo-[4,5-d][1,2,3]triazine-6-amine
  参考文献：
  名称：

  Synthesis of substituted [1,3]thiazolo[4,5-b]pyridines and [1,3]thiazolo[4,5-d][1,2,3]triazines

  摘要：

  In this work, we described an easy preparation Of substituted 4-amino-5-cyano-1,3-thiazoles. These compounds have been used as starting materials to obtain two classes of compounds. New substituted [1,3]thiazolo[4,5-e]pyridines were synthesized in one step via Friedlander reaction. Diazotation of 4-amino-5-cyano-1,3-thiazoles afforded 4-chloro[1,3]thiazolo[4,5-d][1,2,3]triazines in one step. The later Was substituted by a secondary amine to obtain substituted 4-amino[1,3]thiazolo[4,5-d][1,2,3]triazines. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.017
• 作为产物：
  描述：

  4-amino-2-anilino-1,3-thiazole-5-carbonitrile 在 盐酸 、 sodium nitrite 作用下， 以71%的产率得到4-chloro-N-phenyl[1,3]thiazolo[4,5-d][1,2,3]triazine-6-amine
  参考文献：
  名称：

  Synthesis of substituted [1,3]thiazolo[4,5-b]pyridines and [1,3]thiazolo[4,5-d][1,2,3]triazines

  摘要：

  In this work, we described an easy preparation Of substituted 4-amino-5-cyano-1,3-thiazoles. These compounds have been used as starting materials to obtain two classes of compounds. New substituted [1,3]thiazolo[4,5-e]pyridines were synthesized in one step via Friedlander reaction. Diazotation of 4-amino-5-cyano-1,3-thiazoles afforded 4-chloro[1,3]thiazolo[4,5-d][1,2,3]triazines in one step. The later Was substituted by a secondary amine to obtain substituted 4-amino[1,3]thiazolo[4,5-d][1,2,3]triazines. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.017

文献信息

• Design, synthesis, and antitumor screening of new thiazole, thiazolopyrimidine, and thiazolotriazine derivatives as potent inhibitors of VEGFR‐2
  作者：Alaa A. Abd Elhameed、Ahmed R. Ali、Hazem A. Ghabbour、Said M. Bayomi、Nadia S. El‐Gohary

  DOI：10.1002/ddr.22109

  日期：2023.12

  New thiazole, thiazolopyrimidine, and thiazolotriazine derivatives 3–12 and 14a–f were synthesized. The newly synthesized analogs were tested for in vitro antitumor activity against HepG2, HCT-116, MCF-7, HeP-2, and Hela cancer cells. Results indicated that compound 5 displayed the highest potency toward the tested cancer cells. Compound 11b possessed enhanced effectiveness over MCF-7, HepG2, HCT-116

  合成了新的噻唑、噻唑并嘧啶和噻唑并三嗪衍生物3-12和14a-f 。测试了新合成的类似物对 HepG2、HCT-116、MCF-7、HeP-2 和 Hela 癌细胞的体外抗肿瘤活性。结果表明，化合物5对测试的癌细胞表现出最高的效力。化合物11b对 MCF-7、HepG2、HCT-116 和 Hela 癌细胞具有增强的功效。此外，化合物4和6对 HCT-116、MCF-7 和 Hela 癌细胞显示出良好的活性，并对 HepG2 和 HeP-2 细胞显示出卓越的活性。此外，还测试了化合物3-6和11b抑制血管内皮生长因子受体 2 (VEGFR-2) 活性的能力。所得结果表明，化合物5对VEGFR-2表现出显着的抑制活性（半数最大抑制浓度[IC 50 ] = 0.044 μM），与舒尼替尼（IC 50 = 0.100 μM）相当。此外，合成的化合物3-6和11b对 WI38 和 WISH 正常细