2-phenyl-4-(pyridin-3-yl)thiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-4-(pyridin-3-yl)thiazole
• 英文别名: 2-Phenyl-4-pyridin-3-yl-1,3-thiazole
• 化学式: C₁₄H₁₀N₂S
• 分子量: 238.313
• InChiKey: ODKCSOPYXDQUAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(2-溴乙酰基)吡啶氢溴酸盐 、 硫代苯甲酰胺 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到2-phenyl-4-(pyridin-3-yl)thiazole
  参考文献：
  名称：

  Optimization of the aromatase inhibitory activities of pyridylthiazole analogues of resveratrol

  摘要：

  Aromatase is an established target not only for breast cancer chemotherapy, but also for breast cancer chemoprevention. The moderate and non-selective aromatase inhibitory activity of resveratrol (1) was improved about 100-fold by replacement of the ethylenic bridge with a thiadiazole and the phenyl rings with pyridines (e.g., compound 3). The aromatase inhibitory activity was enhanced over 6000-fold by using a 1,3-thiazole as the central ring and modifying the substituents on the 'A' ring to target the Met374 residue of aromatase. On the other hand, targeting the hydroxyl group of Thr310 by a hydrogen-bond acceptor on the 'B' ring did not improve the aromatase inhibitory activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.047

文献信息

• 一种光催化合成噻唑杂环化合物的方法
  申请人：桂林医学院

  公开号：CN110627739B

  公开（公告）日：2023-02-07

  本发明公开了一种光催化合成噻唑杂环化合物的方法，所述方法采用炔烃和硫代酰胺为原料，在吖啶盐的催化下，在空气及室温的条件下，用蓝光灯照射，搅拌后即可得到化噻唑杂环化合物。该方法所用的原料易得，无需过渡金属和其他氧化剂的添加，仅用绿色可持续的可见光引发反应，操作简便，产率可观，环境友好，有良好的应用前景。
• Visible Light-Induced Difunctionalization of Alkynes: The Synthesis of Thiazoles and 1,1-Dibromo-1-en-3-ynes
  作者：Xiaoying Huang、Hui Chen、Zhongzhi Huang、Yanli Xu、Fangyao Li、Xianli Ma、Yanyan Chen

  DOI：10.1021/acs.joc.9b02300

  日期：2019.12.6

  A visible light-induced cascade cyclization of thioamides with alkynes was developed to synthesize 1,3-thiozoles. The sulfur radical generated from thioamide via the single-electron transfer (SET) pathway was promoted by photocatalysis as a key intermediate in this reaction. When bromoalkynes were used as the substrate, the self-coupling products 1,1-dibromo-1-en-3-ynes were obtained in moderate yields

  可见光诱导的硫代酰胺与炔的级联环化反应合成了1,3-噻唑。硫酰胺通过单电子转移（SET）途径生成的硫自由基通过光催化作为该反应的关键中间体而得到促进。当使用溴炔作为底物时，以中等收率获得自偶联产物1,1-dibromo-1-en-3-ynes，并提出了可见光光催化促进该转化的能量转移途径。
• Comparing the Reactivity of the 4- and 5-Positions of 2-Phenylthiazoles in Stille Cross-Coupling Reactions
  作者：Peter Stanetty、Johanna Hämmerle、Michael Schnürch

  DOI：10.1055/s-2007-990972

  日期：2007.12

  A systematic study of the cross-coupling capability of 4- and 5-substituted 2-phenylthiazoles under Stille conditions is presented. Two cross-coupling options were investigated: 1) combination of thiazolylstannanes with various aryl(hetaryl) halides and, 2) reaction of halothiazoles with PhSn(Bu)3 as coupling partner. The results obtained from the cross-coupling reactions on the 4- and 5-positions of the thiazole system were compared regarding the influence of the position of the halide (Br, I) and the Bu3Sn group on both coupling partners. A broad selection of aromatic and heteroaromatic halides was coupled in order to establish a general reactivity platform for this heterocyclic system.

  本文系统研究了在Stille反应条件下4-和5-取代的2-苯基噻唑的交叉偶联能力。研究了两种交叉偶联选项：1）噻唑基锡化物与各种芳基（杂芳基）卤化物的组合；2）以PhSn(Bu)3作为偶联伙伴进行卤噻唑的反应。比较了在噻唑体系的4位和5位上的交叉偶联反应的结果，分析了卤化物（溴、碘）和Bu3Sn基团在两种偶联伙伴上的位置影响。通过偶联大量芳香和杂芳香卤化物，建立了该杂环体系的一般反应性平台。
• A Comparative Study on Stille Cross-Coupling Reactions of 2-Phenylthiazoles and 2-Phenyloxazoles
  作者：Peter Stanetty、Johanna Hämmerle、Markus Spina、Michael Schnürch、Marko Mihovilovic

  DOI：10.1055/s-2008-1067263

  日期：2008.10

  A systematic study of the cross-coupling capability of the 4- and 5-positions of 2-phenylthiazoles and -oxazoles under Stille conditions is presented. The azoles were both applied as stannanes and as the halide component. The obtained results were compared regarding the position of the halide and Bu3Sn group. In order to establish a general reactivity platform for those heterocyclic systems, a broad variety of aromatic and heteroaromatic halides were coupled and some significant differences concerning the coupling properties of the investigated systems were observed.

  本文系统研究了在Stille条件下2-苯基噻唑和-噁唑的4位和5位的交叉偶联能力。噁唑既可用作锡烷，也可用作卤化物成分。将所得结果与卤化物和Bu3Sn基团的位置进行了比较。为了建立这些杂环系统的通用反应平台，对多种芳香和杂芳卤化物进行了偶联，并观察到所研究系统的偶联性质存在一些显著差异。
• Human androgen receptor DNA-binding domain (DBD) compounds as therapeutics and methods for their use
  申请人：The University of British Columbia

  公开号：US10011573B2

  公开（公告）日：2018-07-03

  A compound having the structure of Formula I, wherein A is a substituted or unsubstituted aryl or heteroaryl group, D is a substituted or unsubstituted 5- or 6-membered heteroaryl or heterocyclyl group and E is a substituted or unsubstituted aryl, heteroaryl, cycloalkyl or heterocyclyl group. The compounds are used for the treatment of androgen modulated indications including cancer (prostate, breast, ovarian, endometrial or bladder cancer), hair loss, acne, hirsutism, ovarian cysts, polycystic ovary disease, precocious puberty and age related macular degeneration. The use of the compounds for the manufacture of a medicament for modulating AR activity, a method of treatment using such compounds and a pharmaceutical composition and a commercial package comprising said compounds are also described.

  具有式 I 结构的化合物，其中 A 是取代或未取代的芳基或杂芳基，D 是取代或未取代的 5 或 6 元杂芳基或杂环基，E 是取代或未取代的芳基、杂芳基、环烷基或杂环基。这些化合物可用于治疗雄激素调节适应症，包括癌症（前列腺癌、乳腺癌、卵巢癌、子宫内膜癌或膀胱癌）、脱发、痤疮、多毛症、卵巢囊肿、多囊卵巢病、性早熟和老年性黄斑变性。此外，还描述了这些化合物在制造调节 AR 活性的药物中的用途、使用这些化合物的治疗方法以及包含上述化合物的药物组合物和商业包装。