5-azidocarbonyl-6-methylimidazo[2,1-b][1,3]thiazole | 188561-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并噻唑类
• 英文名称: 5-azidocarbonyl-6-methylimidazo[2,1-b][1,3]thiazole
• 英文别名: 6-methylimidazo[2,1-b][1,3]thiazole-5-carbonyl azide；6-methylimidazo[2,1-b]thiazole-5-carbonyl azide
• CAS: 188561-48-0
• 化学式: C₇H₅N₅OS
• 分子量: 207.216
• InChiKey: VBNLGJZAYVRLRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-azidocarbonyl-6-methylimidazo[2,1-b][1,3]thiazole 在 肼 作用下， 反应 11.0h， 生成 N-(6-methylimidazo[2,1-b][1,3]thiazol-5-yl)hydrazinecarboxamide
  参考文献：
  名称：

  融合杂环：一些新型咪唑噻唑的合成

  摘要：

  研究了带有咪唑 [2, 1-b] [1,3] 噻唑环系统的醛腙或缩氨基脲与巯基链烷酸的反应。使用利福平作为标准，评价由此获得的化合物对结核分枝杆菌H37RV的抗分枝杆菌活性。由于耐多药结核病在临床实践中的兴起，结核病的治疗仍然是主要问题之一。多年来，异烟酸酰肼（异烟肼）一直被用作治疗疾病的主要药物。取代基和生物等排置换对其抗结核活性的影响仍在研究中 (1)。这促使我们合成 6-methylimidazo [2, l-£>] [1, 3] thiazole-5-carbohydrazide 2，异烟肼的结构类似物，及其迄今为止未报道的衍生物，以筛选其抗结核特性。氩气：a，QH5；b,C,;H4F(4); C,QH4C1(4); d、QH4Br(4)；e, QH4CH3 (4) ; f ,QH4OCH3(4) ; g,QH4NO2(2) 6-Methylimidazo[2,1-b][l,3]t

  DOI：

  10.1515/hc.2002.8.5.433
• 作为产物：
  描述：

  6-甲基咪唑并[2,1-B][1,3]噻唑-5-羧肼 在 盐酸 、 sodium nitrite 作用下， 以90%的产率得到5-azidocarbonyl-6-methylimidazo[2,1-b][1,3]thiazole
  参考文献：
  名称：

  甲基的变换大号- （ - ） -噻唑烷-4-羧酸甲酯，2-氨基-2-噻唑啉和2-氨基噻唑成thiazoloazines和azolothiazoles †

  摘要：

  在寻找潜在的免疫调节剂时，将L -（-）-噻唑烷-4-羧酸甲酯（2），2-氨基-2-噻唑啉（12）和2-氨基噻唑（19）转化为各种双环系统的衍生物。因此，由过氢噻唑并[3，4- a ]吡嗪4和5的化合物2衍生物，全氢噻唑并[4，3- c ]-[1，4]恶嗪7和全氢咪唑并[1，5- c ]噻唑9a，b形成。由2,3-二氢噻唑并[2,3- b ]嘧啶13a，b的化合物12衍生物和咪唑并[2,1- b ]噻唑的化合物19衍生物制备21、22、24和25 。6-（对氨基磺酰基苯基）-7-氧杂氢咪唑[1,5- c发现]噻唑-5-硫酮（9a）具有免疫修复活性。

  DOI：

  10.1002/jhet.5570340109

文献信息

• Synthesis of new functionalized imidazo[2,1-b]thiazoles and thiazolo[3,2-a]pyrimidines
  作者：Lucija Peterlin-Mašič、Mateja Malešič、Matej Breznik、AleŠ Krbavčič

  DOI：10.1002/jhet.5570370115

  日期：2000.1

  and 6-methylimidazo[2,1-b]thiazole-5-carboxylic acid (17) were reacted with amines 6a-i by the reaction with oxalyl chloride and N, N-di methyl-formamide as a catalyst into primary and secondary amide derivatives 7-14 and 19-22. From compound 24 N,N'-disubstituted ureas 26, 27 and perhydroimidazo[1,5-c]thiazole 29 derivatives of imidazo[2,1-b]thiazole were prepared. By nmr analysis of compound 29, the

  5-Oxo-5 H- [1,3]噻唑并[3,2 - a ]嘧啶-6-羧酸（4）和6-甲基咪唑并[2,1 - b ]噻唑-5-羧酸（17）通过与草酰氯和作为催化剂的N，N-二甲基甲酰胺的反应，使胺与胺6a-i反应成伯和仲酰胺衍生物7-14和19-22。由化合物24制备N，N′-二取代的脲26、27和咪唑并[2，1- b ]噻唑的全氢咪唑并[ 1，5- c ]噻唑29衍生物。通过化合物的核磁共振分析 由图29可知，存在由C7'a的手性中心引起的旋光性和C5N6 '键的旋转受限引起的构象异构性这两种立体异构体的存在。
• Design, Synthesis and Biological Assessment of N′-(2-Oxoindolin-3-ylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazides as Potential Anti-Proliferative Agents toward MCF-7 Breast Cancer
  作者：Najla A. Alshaye、Mohamed K. Elgohary、Mahmoud S. Elkotamy、Hatem A. Abdel-Aziz

  DOI：10.3390/ph17020216

  日期：——

  Breast cancer is a serious threat to the health and lives of women. Two novel series of N′-(2-oxoindolin-3-ylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazides and 1-(aryl)-3-(6-methylimidazo[2,1-b]thiazol-5-yl)ureas were designed, synthesized and investigated for their anticancer efficacy against the MCF-7 breast cell line. Three compounds of the first series showed potent activity toward MCF-7 with IC50 in the range 8.38–11.67 µM, respectively, as compared to Sorafenib (IC50 = 7.55 µM). N′-(1-butyl-2-oxoindolin-3-ylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide inhibited VEGFR-2 with IC50 = 0.33 µM when compared with Sorafenib (IC50 = 0.09 µM). Furthermore, this compound was introduced to PCR assessment, where it increased Bax, caspase 8, caspase 9 and cytochrome C levels by 4.337-, 2.727-, 4.947- and 2.420-fold, respectively, while it decreased levels of Bcl-2, as the anti-apoptotic gene, by 0.359-fold when compared to the untreated control MCF-7. This compound was also arrested in the G2/M phase by 27.07%, compared with 11.31% for the control MCF-7. Furthermore, it induced early and late apoptosis in MCF-7. In addition, a molecular docking study in the VEGFR-2 active site was performed to assess the binding profile for the most active compounds. Moreover, ADME parameters of the targeted compounds were also evaluated.