ethyl 6-(4-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate | 752244-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 6-(4-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate
• 英文别名: Ethyl 6-(4-nitrophenyl)imidazo[2,1-B][1,3]thiazole-3-carboxylate；ethyl 6-(4-nitrophenyl)imidazo[2,1-b][1,3]thiazole-3-carboxylate
• CAS: 752244-21-6
• 化学式: C₁₄H₁₁N₃O₄S
• 分子量: 317.325
• InChiKey: BRZIWZJAECKVNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 6-(4-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 56.0h， 生成 Tert-butyl 4-[[6-(4-nitrophenyl)imidazo[2,1-b][1,3]thiazol-3-yl]methyl]piperazine-1-carboxylate
  参考文献：
  名称：

  Search for a novel SIRT1 activator: Structural modification of SRT1720 and biological evaluation

  摘要：

  Syntheses and biological evaluation of novel SRT1720 derivatives are described in search for new candidates of SIRT1 activator. Several parts of the SRT1720 structure, including piperazine moiety, quinoxaline ring on the amide group, and position of the amide function, were modified, and the assay results indicated that transfer of the ortho amide-substituent regarding to the imidazo[1,2-b]thiazole core onto the meta position resulted in improvement of SIRT1 activation ability. Modeling analyses of SRT1720 and the most potent derivative bound to model complex of SIRT1 with peptide substrate were also performed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.070
• 作为产物：
  描述：

  2-氨基噻唑-4-甲酸乙酯 在 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成 ethyl 6-(4-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate
  参考文献：
  名称：

  Khazi; Koti; Gadad, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 2, p. 393 - 398

  摘要：

  DOI：

文献信息

• Discovery of 6-phenylimidazo[2,1-b]thiazole derivatives as a new type of FLT3 inhibitors
  作者：Xing-Dong Lin、Hui-Wen Yang、Shuang Ma、Wei-Wei Li、Chun-Hui Zhang、Wen-Jing Wang、Rong Xiang、Lin-Li Li、Sheng-Yong Yang

  DOI：10.1016/j.bmcl.2015.08.068

  日期：2015.10

  In this investigation, a series of 6-phenylimidazo[2,1-b] thiazole derivatives were synthesized. Structure-activity relationship (SAR) analysis of these compounds based on cellular assays led to the discovery of a number of compounds that showed potent activity against FLT3-dependent human acute myeloid leukemia (AML) cell line MV4-11, but very weak or no activity against FLT3-independent human cervical cancer cell line Hela. FLT3 kinase inhibition assays were then performed on the three most active compounds. Among these compounds, 6-(4-(3-(5-(tert-butyl)isoxazol- 3-yl)ureido)phenyl)-N-(3-(dimethylamino)propyl)imidazo[2,1-b]thiazole-3-carboxamide (19) exhibited the highest potency in both cellular (MV4-11, IC50: 0.002 mu M) and enzymatic (FLT3, IC50: 0.022 mu M) assays. Further in-depth in vitro anti-AML activity and mechanism of action studies were carried out on compound 19. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of Ethyl 8‐Aryl‐8‐hydroxy‐3‐oxo‐8<i>H</i>[1,2,4]oxadiazolo‐[3,4‐<i>c</i>][1,4]thiazine‐5‐carboxylates by Ring‐Expansion Rearrangement
  作者：Rajesh Koti、Vinayak Hegde、Gundurao Kolavi,、Imtiyaz Ahmed Khazi

  DOI：10.1080/00397910701265945

  日期：2007.5.1

  The title compounds were prepared by the ring-ring interconversion of ethyl 5-nitroso-6-arylimidazo[2,1-b] thiazole-3-carboxylates with hydrochloric acid. The effect of electron-withdrawing substituent in the thiazole ring on the general applicability of the ring-ring interconversion has been also evaluated.
• Search for a novel SIRT1 activator: Structural modification of SRT1720 and biological evaluation
  作者：Yuji Matsuya、Yuta Kobayashi、Sayumi Uchida、Yukihiro Itoh、Hideyuki Sawada、Takayoshi Suzuki、Naoki Miyata、Kenji Sugimoto、Naoki Toyooka

  DOI：10.1016/j.bmcl.2013.06.070

  日期：2013.9

  Syntheses and biological evaluation of novel SRT1720 derivatives are described in search for new candidates of SIRT1 activator. Several parts of the SRT1720 structure, including piperazine moiety, quinoxaline ring on the amide group, and position of the amide function, were modified, and the assay results indicated that transfer of the ortho amide-substituent regarding to the imidazo[1,2-b]thiazole core onto the meta position resulted in improvement of SIRT1 activation ability. Modeling analyses of SRT1720 and the most potent derivative bound to model complex of SIRT1 with peptide substrate were also performed. (C) 2013 Elsevier Ltd. All rights reserved.
• Khazi; Koti; Gadad, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 2, p. 393 - 398
  作者：Khazi、Koti、Gadad、Mahajanshetti、Shivakumar、Akki

  DOI：——

  日期：——