1-(4-氯苯基)-3-甲基硫脲 | 2740-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-氯苯基)-3-甲基硫脲
• 英文名称: 1-(4-chlorophenyl)-3-methylthiourea
• CAS: 2740-97-8
• 化学式: C₈H₉ClN₂S
• mdl: MFCD02940753
• 分子量: 200.692
• InChiKey: UKOJOHPYEVWPNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)-3-甲基硫脲 在 哌啶 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 (5Z)-5-(3-chloro-5-ethoxy-4-hydroxybenzylidene)-2-(4-chlorophenylimino)-3-methylthiazolidin-4-one
  参考文献：
  名称：

  HL005—A new selective PPARγ antagonist specifically inhibits the proliferation of MCF-7

  摘要：

  Peroxisome proliferator-activated receptor-gamma (PPAR gamma) is a nuclear transcription factor which is involved in many diseases, such as diabetes, inflammation, dyslipidemia. hypertension, and cancer. Recently, there are many reports showing that PPAR gamma agonists have preclinical and clinical anticancer activity, with relatively few reports on anticancer effects of PPAR gamma antagonists. From our compound library, a novel 3-thiazolinone-modified benzoic acid derivative HL005 is found as PPAR gamma selective ligand through SPR analysis (K-D = 0.21 mu M), yeast two-hybrid results suggest that HL005 antagonize the potent PPAR gamma agonist rosiglitazone-induced recruitment of the coactivator for PPAR gamma (IC50 = 7.97 mu M). Different from the most reported PPAR gamma antagonist, HL005 can inhibit the proliferation of MCF-7 cell line in a concentration-dependent manner and induce cell cycle arrest at G2/M phase, other than interference with cell adhesion. In order to study the binding mode of this compound, three derivatives are synthesized to get more detail about the structure-activity relationship, molecular docking and the NMR spectra indicate that similar to most PPAR gamma ligand, the carboxylic acid group is an important moiety for HL005 and contributes strong interaction with PPAR gamma. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jsbmb.2011.01.019
• 作为产物：
  描述：

  N,N'-dimethylthioperoxydicarbamic acid 、 对氯苯胺 以 乙醇 为溶剂， 生成 1-(4-氯苯基)-3-甲基硫脲
  参考文献：
  名称：

  Nair,G.V., Journal of the Indian Chemical Society, 1965, vol. 42, p. 359 - 366

  摘要：

  DOI：

文献信息

• Nickel Catalysis Enables Access to Thiazolidines from Thioureas via Oxidative Double Isocyanide Insertion Reactions
  作者：Wen-Kui Yuan、Yan Fang Liu、Zhenggang Lan、Li-Rong Wen、Ming Li

  DOI：10.1021/acs.orglett.8b03098

  日期：2018.11.16

  Ni-catalyzed oxidative double isocyanide insertion to thioureas under air conditions, in which thioureas play three roles as a substrate, a ligand, and overcoming isocyanide polymerization. The reaction is featured by employing a low-cost and low loading Ni(acac)2 catalyst, without any additives, and high atom economy. This is the first example to directly apply a Ni(II) catalyst in oxidative double isocyanide

  通过在空气条件下将Ni催化的氧化双异氰酸酯插入硫脲中，开发了噻唑烷2,4,5-三亚胺衍生物的有效合成方法，其中硫脲起底物，配体和克服异氰酸酯聚合的三类作用。该反应的特点是采用低成本，低负荷的Ni（acac）2催化剂，不添加任何添加剂，并且具有高原子经济性。这是在氧化双异氰酸酯插入反应中直接应用Ni（II）催化剂的第一个示例。
• Quantitative Solid-State Reactions of Amines with Carbonyl Compounds and Isothiocyanates
  作者：Gerd Kaupp、Jens Schmeyers、Juergen Boy

  DOI：10.1016/s0040-4020(00)00511-1

  日期：2000.9

  solid anhydrides to give diamides (therefrom imides) or amidic carboxylic salts or imides, with solid imides to give diamides, with solid lactones or carbonates to give functionalized carbamic esters, with polycarbonates to give degradative aminolysis, and with solid isothiocyanates to give thioureas. Diamides give imides by solid-state thermolysis or acid catalysis. Various double, two-step, 3-cascade

  据报道，气态或固态胺与醛的一系列固相反应生成亚胺，固态酸酐生成二酰胺（由酰亚胺生成）或酰胺羧酸盐或酰亚胺，固态酰亚胺生成二酰胺，与固态内酯或碳酸盐生成固态反应。得到官能化的氨基甲酸酯，与聚碳酸酯得到降解的氨解，和与固体异硫氰酸酯得到硫脲。二酰胺通过固态热解或酸催化作用生成酰亚胺。据报道，各种双反应，两步反应，3级反应和顺序反应均处于固态而不熔化。在53个已报告的反应实例中，产率是定量的，并且在100％产率的反应中无需进行后处理（除了四次洗涤）。最初的三个固态反应但与液态产物的反应不是定量的。升至公斤级显示了该技术在大规模应用中的前景。原子力显微镜的超显微分析通过三步法中影响深远的各向异性分子运动阐明了固态机制。还使用AFM研究了聚碳酸酯的气固氨基分解酶。讨论了对可持续化学的影响。
• Efficient synthesis of 5-(2-hydroxyethyl)-2-phenylimino- 1,3-thiazolidin-4-ones and 5-(2-hydroxyethyl)-2-phenylamino-4,5-dihydro-1,3-thiazol-4-ones
  作者：Jiří Váňa、Jiří Hanusek、Aleš Růžička、Miloš Sedlák

  DOI：10.1002/jhet.118

  日期：2009.7

  A new method for the synthesis of substituted 5-(2-hydroxyethyl)-2-phenylimino-1,3-thiazolidin-4-ones and 5-(2-hydroxyethyl)-2-phenylamino-4,5-dihydro-1,3-thiazol-4-ones is described, starting from phenylthioureas and 3-bromotetrahydrofuran-2-one. The reaction proceeds under mild conditions, is very simple to perform, and is applicable to a relatively wide range of substituents in benzene nucleus.

  一种合成取代的5-（2-羟乙基）-2-苯基亚氨基-1,3-噻唑烷酮-4-酮和5-（2-羟乙基）-2-苯基氨基-4,5-二氢-1的新方法，描述了3-噻唑-4-酮，其起始于苯硫脲和 3-溴四氢呋喃-2-酮。该反应在温和的条件下进行，非常容易进行，并且适用于苯核中相对广泛的取代基。由于质子互变异构和E- / Z-立体异构，一些1,3-噻唑烷-4-酮在溶液中表现出动态NMR行为。J.杂环化​​学，（2009）。
• A Facile Synthesis of 2-N(Methyl Amino) Benzothiazoles
  作者：Narahari Babu Ambati、V. Anand、P. Hanumanthu

  DOI：10.1080/00397919708006084

  日期：1997.5

  Abstract Reaction of aromatic primary amines with methylisothiocyanate (MITC) yielded N-methyl-N1-(benzelene-1-yl)thioureas which underwent oxidative cyclization in the presence of bromine in acetic acid, at room temperature, affording the title compounds.

  摘要 芳香伯胺与甲基异硫氰酸酯 (MITC) 反应生成 N-甲基-N1-(benzelene-1-yl) 硫脲，在溴存在下，在乙酸中，室温下进行氧化环化，得到标题化合物。
• Thiazoline derivatives
  申请人：Hoechst Aktiengesellschaft

  公开号：US04346088A1

  公开（公告）日：1982-08-24

  Thiazoline derivatives of the general formula I ##STR1## wherein R.sup.1 to R.sup.7 have the specified meanings, physiologically acceptable acid addition salts thereof, processes for their preparation, pharmaceutical preparations based on these compounds and their use for acting on the serum lipoprotein spectrum. The invention moreover relates to compounds of the formulae ##STR2## wherein A, R, R.sup.1 to R.sup.7, Y and Z have the specified meanings.

  通式I的噻唑啉衍生物##STR1##，其中R.sup.1至R.sup.7具有指定的含义，其生理上可接受的酸盐，其制备方法，基于这些化合物的制药制剂以及它们用于作用于血清脂蛋白谱的用途。此外，本发明涉及以下通式的化合物##STR2##，其中A，R，R.sup.1至R.sup.7，Y和Z具有指定的含义。