(6-苯基咪唑并[2,1-b][1,3]噻唑-5-基)甲醇 | 76919-41-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (6-苯基咪唑并[2,1-b][1,3]噻唑-5-基)甲醇
• 英文名称: 5-idrossimetil-6-fenilimidazo<2,1-b>tiazolo
• 英文别名: (6-Phenylimidazo[2,1-b][1,3]thiazol-5-yl)methanol
• CAS: 76919-41-0
• 化学式: C₁₂H₁₀N₂OS
• mdl: MFCD02253178
• 分子量: 230.29
• InChiKey: AGNXXFZBPOCOPO-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200°
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  (6-苯基咪唑并[2,1-b][1,3]噻唑-5-基)甲醇 在 五氯化磷 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 5.0h， 生成 5-cyanomethyl-6-phenylimidazo<2,1-b>thiazole
  参考文献：
  名称：

  Andreani, Aldo; Leoni, Alberto; Locatelli, Alessandra, Arzneimittel-Forschung/Drug Research, 2000, vol. 50, # 6, p. 550 - 553

  摘要：

  DOI：
• 作为产物：
  描述：

  6-苯基-咪唑并[2,1-b]噻唑-5-甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (6-苯基咪唑并[2,1-b][1,3]噻唑-5-基)甲醇
  参考文献：
  名称：

  Andreani, A.; Bonazzi, D.; Rambaldi, M., Farmaco, Edizione Scientifica, 1980, vol. 35, # 11, p. 896 - 901

  摘要：

  DOI：

文献信息

• Potential anti-tumor agents XVI. Imidazo[2,1-b]thiazoles
  作者：A ANDREANI、M RAMBALDI、F ANDREANI、R BOSSA、I GALATULAS

  DOI：10.1016/0223-5234(88)90214-0

  日期：1988.7
• Effects of new ubiquinone-imidazo[2,1-b]thiazoles on mitochondrial complex I (NADH-ubiquinone reductase) and on mitochondrial permeability transition pore
  作者：Aldo Andreani、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Maurizio Recanatini、Giorgio Lenaz、Romana Fato、Christian Bergamini

  DOI：10.1016/j.bmc.2004.08.012

  日期：2004.11

  In this work we describe the synthesis of a series of imidazo[2,1-b]thiazoles and 2,3-dihydroimidazo[2,1-b]thiazoles connected by means of a methylene bridge to CoQ(0). These compounds were tested as specific inhibitors of the NADH:ubiquinone reductase activity in mitochondrial membranes. The imidazothiazole system when bound to the quinone ring in place of the isoprenoid lateral side chain, may increase the inhibitory effect (with an IC50 for NADH-Q(1) activity ranging between 0.25 and 0.96 muM) whereas the benzoquinone moiety seems to lose the capability to accept electrons from complex I as indicated by very low maximal velocity elicited by the compounds tested. Moreover the low rotenone sensitivity for almost all of these compounds suggests that they are only partially able to interact with the physiological ubiquinone-reduction site. The compounds were investigated for the capability of increasing the permeability transition of the inner mitochondrial membrane in isolated mitochondria. Unlike CoQ(0), which is considered a mitochondrial membrane permeability transition inhibitor, the new compounds were inducers. (C) 2004 Elsevier Ltd. All rights reserved.
• ANDREANI A.; BONAZZI D.; RAMBALDI M., FORMACO. ED. SCI., 1980, 35, NO 11, 896-901
  作者：ANDREANI A.、 BONAZZI D.、 RAMBALDI M.

  DOI：——

  日期：——
• ANDREANI, ALDO;RAMBALDI, MIRELLA;ANDREANI, FRANCO;BOSSA, ROSARIA;GALATULA+, EUR. J. MED. CHEM., 23,(1988) N 4, C. 385-389
  作者：ANDREANI, ALDO、RAMBALDI, MIRELLA、ANDREANI, FRANCO、BOSSA, ROSARIA、GALATULA+

  DOI：——

  日期：——
• CAR ACTIVATOR AGENTS FOR CYCLOPHOSPHAMIDE-BASED TREATMENTS OF CANCER
  申请人：UNIVERSITY OF MARYLAND, BALTIMORE

  公开号：US20200352915A1

  公开（公告）日：2020-11-12

  The invention relates to selective small molecule human constitutive androstane receptor (hCAR) activators of Formula (I) or (II), pharmaceutical compositions thereof, and use thereof for the treatment of hematologic malignancies and other cancers. The small molecule hCAR activator in combination with CPA based chemotherapy regimen provides a synergistic effect to help promote cytoxicity of the cyclophosphamide (CPA) based anticancer treatments including CHOP regimen (CPA, doxorubicin, vincristine, and prednisone) by preferential induction of CYP2B6 over CYP3A4 and promoting the formation of therapeutically active CPA metabolite 4-OH-CPA.