4,4,5-trifluoro-2,5-diphenyl-4,5-dihydrothiazole | 1362243-68-2

• 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: 4,4,5-trifluoro-2,5-diphenyl-4,5-dihydrothiazole
• 英文别名: 2,5-Diphenyl-4,4,5-trifluoro-4,5-dihydrothiazole；4,4,5-trifluoro-2,5-diphenyl-1,3-thiazole
• CAS: 1362243-68-2
• 化学式: C₁₅H₁₀F₃NS
• 分子量: 293.312
• InChiKey: HRQLPHSRWXSTMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,5-diphenyl-1,3-thiazole 在 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以24%的产率得到4,4,5-trifluoro-2,5-diphenyl-4,5-dihydrothiazole
  参考文献：
  名称：

  三氟噻唑啉支架导致靶向促胰蛋白酶的促凋亡药物。

  摘要：

  合成了具有前所未有的三氟噻唑啉骨架的一类新的小分子，并评估了它们的促凋亡活性。EC 50处于低微摩尔范围内，无论p53的功能状态如何，这些化合物均被证明是在广泛的肿瘤细胞系中凋亡的有效诱导剂。快速的结构-活性关系研究允许制备最强的凋亡诱导候选物。使用高性能亲和纯化方法，我们确定了抑制素1和2，涉及维持细胞生存力的关键蛋白质，作为这些化合物的目标。

  DOI：

  10.1002/anie.201405758

文献信息

• FLUORINATED THIAZOLES FOR USE IN TREATING CANCER
  申请人：Gil Santano Joan

  公开号：US20130190367A1

  公开（公告）日：2013-07-25

  Compounds of formula (I) or their pharmaceutically acceptable salts, or their stereoisomers or mixtures of stereoisomers, where: R 1 is selected from the group consisting of: phenyl, and phenyl mono-, di-, or tri-substituted by a radical independently selected from the group consisting of F, Cl, Br, I, (C 1 -C 6 )-alkyl, COO-(C 1 -C 6 )-alkyl, and (C 1 -C 6 )-alkoxy; and R 2 is a radical selected from the same group as R 1 , further including a phenyl substituted in 4-position by a radical independently selected from the group consisting of —O(CH 2 )CONH(CH 2 ) 3 CH 3 and OCH 2 COOC(CH 3 ) 3 , a biphenyl-4-yl, thiazol-2-yl, and a thiazol-2-yl mono- or di-substituted by a radical selected from F and phenyl; inhibit cell proliferation of tumor cells independently of p53 protein and may also induce apoptosis in several tumor cells independently of p53 protein, being useful for the treatment of several types of cancer.

  式(I)的化合物或其药学上可接受的盐，或其立体异构体或立体异构体混合物，其中：R1选自以下群组：苯基，以及苯基单、双、或三位上由以下基团中独立选择的基团取代：F、Cl、Br、I、(C1-C6)-烷基、COO-(C1-C6)-烷基和(C1-C6)-烷氧基；而R2是从与R1相同的群组中选择的基团，还包括在4位上由以下基团中独立选择的基团取代的苯基：—O(CH2)CONH(CH2)3CH3和OCH2COOC(CH3)3，联苯基-4-基、噻唑-2-基和噻唑-2-基单或双取代的基团中选择F和苯基的化合物，独立于p53蛋白质抑制肿瘤细胞增殖，也可能在几种独立于p53蛋白质的肿瘤细胞中诱导凋亡，可用于治疗多种类型的癌症。
• Mono- and trifluorination of the thiazole ring of 2,5-diarylthiazoles using N-fluorobenzenesulfonimide (NFSI)
  作者：Julie M. Hatfield、Cheryl K. Eidell、Chad E. Stephens

  DOI：10.1016/j.tetlet.2012.12.052

  日期：2013.2

  Fluorination of select 2,5-diarylthiazoles using the N-F reagent N-fluorobenzenesulfonimide (NFSI) has led to the formation of both the anticipated 4-fluorothiazole as well as a unique 4,4,5-trifluorothiazole. Selective monofluorination is best achieved using bromobenzene as solvent at 155 degrees C, while trifluorination is best achieved by performing the reaction without solvent at 135-140 degrees C. An X-ray crystal structure has been obtained on one of the trifluorinated products. (C) 2012 Elsevier Ltd. All rights reserved.
• US8680126B2
  申请人：——

  公开号：US8680126B2

  公开（公告）日：2014-03-25
• A Trifluorinated Thiazoline Scaffold Leading to Pro-apoptotic Agents Targeting Prohibitins
  作者：Alba Pérez-Perarnau、Sara Preciado、Claudia Mariela Palmeri、Cristina Moncunill-Massaguer、Daniel Iglesias-Serret、Diana M. González-Gironès、Miriam Miguel、Satoki Karasawa、Satoshi Sakamoto、Ana M. Cosialls、Camila Rubio-Patiño、José Saura-Esteller、Rosario Ramón、Laia Caja、Isabel Fabregat、Gabriel Pons、Hiroshi Handa、Fernando Albericio、Joan Gil、Rodolfo Lavilla

  DOI：10.1002/anie.201405758

  日期：2014.9.15

  A new class of small molecules, with an unprecedented trifluorothiazoline scaffold, were synthesized and their pro‐apoptotic activity was evaluated. With an EC50 in the low micromolar range, these compounds proved to be potent inducers of apoptosis in a broad spectrum of tumor cell lines, regardless of the functional status of p53. Fast structure–activity relationship studies allowed the preparation

  合成了具有前所未有的三氟噻唑啉骨架的一类新的小分子，并评估了它们的促凋亡活性。EC 50处于低微摩尔范围内，无论p53的功能状态如何，这些化合物均被证明是在广泛的肿瘤细胞系中凋亡的有效诱导剂。快速的结构-活性关系研究允许制备最强的凋亡诱导候选物。使用高性能亲和纯化方法，我们确定了抑制素1和2，涉及维持细胞生存力的关键蛋白质，作为这些化合物的目标。