(E)-3-phenylprop-2-enethioamide | 20314-83-4

• 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: (E)-3-phenylprop-2-enethioamide
• 英文别名: thiocinnamamide；3t-phenyl-thioacrylamide；trans-thiocinnamic acid amide；trans-Thiozimtsaeure-amid；trans-Thiozimtsaeureamid；trans-Thiocinnamamid；3-Phenylprop-2-enethioamide
• CAS: 20314-83-4
• 化学式: C₉H₉NS
• 分子量: 163.243
• InChiKey: HIJXCSPSAVIBMJ-VOTSOKGWSA-N

物化性质

• 沸点：
  297.8±33.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-phenylprop-2-enethioamide 在 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (E)-N-hydroxy-4-(2-styrylthiazol-4-yl)butanamide
  参考文献：
  名称：

  Computer-aided identification of new histone deacetylase 6 selective inhibitor with anti-sepsis activity

  摘要：

  Histone deacetylase (HDAC) inhibitors have been recognized as promising approaches to the treatment of various human diseases including cancer, inflammation, neurodegenerative diseases, and metabolic disorders. Several pan-HDAC inhibitors are currently approved only as anticancer drugs. Interestingly, SAHA (vorinostat), one of clinically available pan-HDAC inhibitors, shows an anti-inflammatory effect at concentrations lower than those required for inhibition of tumor cell growth. It was also reported that HDAC6 selective inhibitor tubastatin A has anti-inflammatory and anti-rheumatic effect. In our efforts to develop novel HDAC inhibitors, we rationally designed various HDAC inhibitors based on the structures of two hit compounds identified by virtual screening of chemical database. Among them, 9a ((E)-N-hydroxy-4-(2-styrylthiazol-4-yl)butanamide) was identified as a HDAC6 selective inhibitor (IC50 values of 0.199 mu M for HDAC6 versus 13.8 mu M for HDAC1), and it did not show significant cytotoxicity against HeLa cells. In vivo biological evaluation of 9a was conducted on a lipopolysaccharide (LPS)-induced mouse model of sepsis. The compound 9a significantly improved 40% survival rate (P = 0.0483), and suppressed the LPS-induced increase of TNF-alpha and IL-6 mRNA expression in the liver of mice. Our study identified novel HDAC6 selective inhibitor 9a, which may serve as a potential lead for the development of anti-inflammatory or anti-sepsis agents. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.046
• 作为产物：
  描述：

  反-肉桂酰胺 在 1,4-二氧六环 、 phosphorous (V) sulfide 作用下， 生成 (E)-3-phenylprop-2-enethioamide
  参考文献：
  名称：

  关于噻唑化合物中2位甲基的缩合能力

  摘要：

  1.已经使用许多实例测试了2-甲基噻唑化合物与苯甲醛的缩合能力，包括2-甲基噻唑，并且由此获得的2-苯乙烯基噻唑化合物的结构已经通过从肉桂酸硫酰胺和卤代羰基化合物直接合成来证明。

  DOI：

  10.1002/hlca.19480310421

文献信息

• Single-Step Microwave-Mediated Synthesis of Oxazoles and Thiazoles from 3-Oxetanone: A Synthetic and Computational Study
  作者：David Orr、Alexandra Tolfrey、Jonathan M. Percy、Joanna Frieman、Zoë A. Harrison、Matthew Campbell-Crawford、Vipulkumar K. Patel

  DOI：10.1002/chem.201301011

  日期：2013.7.15

  The direct microwave‐mediated condensation between 3‐oxetanone and primary amides and thioamides has delivered moderate to good yields of (hydroxymethyl)oxazoles and (hydroxymethyl)thiazoles. The reactions use a sustainable solvent and only require short reaction times. These are highly competitive methods for the construction of two classes of valuable heteroarenes, which bear a useful locus for further

  3-氧杂环丁酮与伯酰胺和硫代酰胺之间的直接微波介导缩合反应产生了中等到良好的（羟甲基）恶唑和（羟甲基）噻唑收率。反应使用可持续的溶剂，只需要很短的反应时间。这些是构建两类有价值的杂芳烃的高度竞争性方法，它们具有进一步阐明的有用位置。电子结构计算表明，事件的顺序涉及sp 3处硫属元素原子的攻击碳和烷基-氧裂解。清楚地表明了酸催化的关键作用，并证明了酸强度的重要性。计算的势垒也与所观察到的硫酰胺和酰胺反应性顺序完全一致。自发的开环涉及适度的CO裂解，减缓了应力释放的程度。在酸催化的途径上，CO的裂解仍然不太广泛，但是通过羧酸催化剂，质子转移到核反应堆中的进展非常快，而基本上是用甲磺酸完成的。
• Structure-activity relationship study of thiazolyl-hydroxamate derivatives as selective histone deacetylase 6 inhibitors
  作者：Gibeom Nam、Jun Min Jung、Hyun-Ju Park、Seung Yeop Baek、Ki Seon Baek、Hui yeon Mok、Da Eun Kim、Young Hoon Jung

  DOI：10.1016/j.bmc.2019.06.036

  日期：2019.8

  autoimmune disease therapeutics. In a previous study, we developed the novel HDAC6-selective inhibitor 9a ((E)-N-hydroxy-4-(2-styrylthiazol-4-yl)butanamide) and showed that it has anti-sepsis activity in vivo. In this study, we conducted structure-activity relationship (SAR) studies to optimize the activity and selectivity of HDAC6, synthesizing its derivatives with various aliphatic linker sizes and cap

  几种人类疾病与组蛋白脱乙酰基酶（HDACs）介导的异常表观遗传途径有关，尤其是IIb类HDACs HDAC6，已成为神经退行性疾病和自身免疫性疾病治疗方法的引人注目的靶标。在以前的研究中，我们开发了新型的HDAC6-选择性抑制剂9a（（E）-N-羟基-4-（2-苯乙烯基噻唑-4-基）丁酰胺），并显示其在体内具有防腐作用。在这项研究中，我们进行了结构-活性关系（SAR）研究，以优化HDAC6的活性和选择性，并合成具有各种脂肪族接头尺寸和帽结构的HDAC6衍生物。我们确定了6u（（E）-N-羟基-3-（2-（4-氟苯乙烯基）噻唑-4-基）丙酰胺），具有纳摩尔抑制活性，对HDAC6的选择性是HDAC1的126倍。通过对HDAC亚型6u的对接分析，我们揭示了最佳脂族连接基大小的重要性，以及芳基帽基团的电子取代作用和刚性。因此，我们建议设计HDAC6选择性抑制剂的新原理。
• One-Step Synthesis of Methanesulfonyloxymethyl Ketones<i>via</i>Gold-Catalyzed Oxidation of Terminal Alkynes: A Combination of Ligand and Counter Anion Enables High Efficiency and a One-Pot Synthesis of 2,4-Disubstituted Thiazoles
  作者：Gongde Wu、Renhua Zheng、Jonathan Nelson、Liming Zhang

  DOI：10.1002/adsc.201300855

  日期：2014.4.14

  Mor‐DalPhos as the P,N‐bidentate ligand and mesylate as the counter ion, the resulting gold(I) complex catalyzes efficient oxidative transformations of various terminal alkynes into synthetically versatile methanesulfonyloxymethyl ketones. The mild reaction conditions and high efficiency permit the one‐pot synthesis of a range of valuable 2,4‐disubstituted thiazoles by subjecting the resulting reaction

  通过使用Mor-DalPhos作为P，N-双齿配体和甲磺酸酯作为抗衡离子，所得的Gold（I）络合物催化各种末端炔烃高效氧化转化为合成用途的甲磺酰氧基甲基酮。温和的反应条件和高效率可通过使所得的反应混合物在温和的条件下与硫酰胺进一步缩合，一锅法合成一系列有价值的2,4-二取代的噻唑。
• Oxazolidinedione derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05932601A1

  公开（公告）日：1999-08-03

  2,4-Oxazolidinedione derivative represented by the formula: ##STR1## wherein R stands for an optionally substituted hydrocarbon residue or heterocyclic group; Y stands for a group represented by --CO--, --CH(OH)-- or --NR.sup.3 -- (wherein R.sup.3 stands for an optionally substituted alkyl group); m is 0 or 1; n is 0, 1 or 2; A stands for a C.sub.1-7 divalent aliphatic hydrocarbon group; R.sup.1 stands for hydrogen or an alkyl group; ring E stands for a benzene ring having 1 or 2 substituents; L and M respectively stand for hydrogen, or L and M may optionally be combined with each other to form a bond; with a proviso that the partial formula: ##STR2## does not include the formula: ##STR3## wherein R' stands for an alkyl group; or a salt thereof, which has excellent actions of lowering blood sugar and lipid in blood.

  该公式代表的2,4-噁唑烷二酮衍生物：其中R代表可选择取代的碳氢残基或杂环基团；Y代表一个由--CO--, --CH(OH)--或--NR.sup.3--（其中R.sup.3代表可选择取代的烷基基团）表示的基团；m为0或1；n为0, 1或2；A代表一个C.sub.1-7二价脂肪族碳氢基团；R.sup.1代表氢原子或烷基基团；环E代表具有1或2个取代基的苯环；L和M分别代表氢原子，或L和M可以选择性地结合在一起形成一个键；但是，部分公式不包括公式：其中R'代表烷基基团；或其盐，具有降低血糖和血脂的优秀作用。
• Amidine derivatives as selective antagonists of ndma receptors
  申请人：——

  公开号：US20030119871A1

  公开（公告）日：2003-06-26

  A class of styryl amidine derivatives which are antagonists of the hum NMDA receptor, being selective for those containing the NR2B subunit, are active in the treatment and/or prevention of neurological and neurodegenerative disorders, in particular neuropathic pain and headache, specifically migraine, whils displaying fewer ataxic and related side-effects associated with other classes of NMDA receptor antagonists.

  一类styryl amidine衍生物，它们是hum NMDA受体的拮抗剂，对含有NR2B亚基的受体具有选择性，在治疗和/或预防神经系统和神经退行性疾病方面具有活性，特别是神经病性疼痛和头痛，特别是偏头痛，同时显示出更少的共济失调和其他NMDA受体拮抗剂相关的副作用。