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.
• FUSED HETEROCYCLES : SYNTHESIS OF SOME NEW IMIDAZOTHIAZOLES
  作者：Nesrin Cesur、Zafer Cesur、Handan Guner、B. Ozden Kasimoğullari

  DOI：10.1515/hc.2002.8.5.433

  日期：2002.1

  Reaction of aldehyde-hydrazones or semicarbazones bearing an imidazo [2, 1-b] [1,3]thiazole ring system with mercaptoalkanoic acids were investigated. Antimycobacterial activities of compounds thus obtained were evaluated against Mycobacterium tuberculosis H37RV using rifampine as standard. Treatment of tuberculosis is still one of the major problems due to the rise of multidrug resistant tuberculosis

  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
• Transformations of methyl<i>L</i>-(-)-thiazolidine-4-carboxylate, 2-amino-2-thiazoline and 2-aminothiazole into thiazoloazines and azolothiazoles
  作者：Mateja Malešíč、Aleš Krbačič、Branko Stanovnik

  DOI：10.1002/jhet.5570340109

  日期：1997.1

  In the search for potential immunomodulators methyl L-(—)-thiazolidine-4-carboxylate (2), 2-amino-2-thiazoline (12), and 2-aminothiazole (19) were transformed into derivatives of various bicyclic systems. Thus, from compound 2 derivatives of perhydrothiazolo[3,4-a]pyrazine 4 and 5, perhydrothiazolo[4,3-c]-[1,4]oxazine 7, and perhydroimidazo[1,5-c]thiazole 9a,b, from compound 12 derivatives of 2,3-dihydro-thiazolo[2

  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。