2-methyl-4-styrylthiazole | 91396-81-5

• 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: 2-methyl-4-styrylthiazole
• 英文别名: 2-methyl-4-trans-styryl-thiazole；2-Methyl-4-trans-styryl-thiazol；2-methyl-4-[(E)-2-phenylethenyl]-1,3-thiazole
• CAS: 91396-81-5
• 化学式: C₁₂H₁₁NS
• 分子量: 201.292
• InChiKey: BEXFLJHBLOMGSU-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,4-三唑-3,5-二酮 、 2-methyl-4-styrylthiazole 生成 4-Methyl-8-phenyl-3-thia-1,5,9,11-tetrazatricyclo[7.3.0.02,6]dodeca-4,6-diene-10,12-dione
  参考文献：
  名称：

  4-烯基噻唑与1,2,4-三唑啉-3,5-二酮的极性杂Diels-Alder反应：实验和计算研究

  摘要：

  4-链烯基噻唑与4-苯基-1,2,4-三唑啉-3,5-二酮（PTAD）的杂Diels-Alder反应可通过独特的表面方法以优异的收率和高水平的立体控制产生新的杂多环系统。立体异构中心位于烯基取代基上的4-烯基噻唑与PTAD反应，得到适度非对映异构体过量的相应手性环加合物。立体化学过程由两个非对映异构过渡态的空间相互作用决定。用结构上较简单的试剂对这些过程进行了计算研究。对于2-未取代的4-乙烯基和4-苯乙烯基噻唑，优选通过高度异步过渡态的协同途径。但是，有两种替代的，同样可能的途径，即协调一致的和循序渐进的，已发现随后是2-甲基或2-苯基取代的4-苯乙烯基噻唑。协调的路径具有高度异步的过渡状态。对于逐步路径，速率确定步骤是第一个步骤，因为实际上不存在第二个步骤的能垒。

  DOI：

  10.1021/jo7021668
• 作为产物：
  描述：

  羟基甲苯磺酰碘苯 以 乙醇 、 二氯甲烷 为溶剂， 生成 2-methyl-4-styrylthiazole
  参考文献：
  名称：

  HTIB-Mediated One-Pot Synthesis of Some 2-Substituted 4-Styrylthiazoles from (E)-4-Arylbut-3-en-2-ones

  摘要：

  The reaction of (E)-4-arylbut-3-en-2-ones with [(hydroxy(tosyloxy)iodo]benzene (HTIB) followed by treatment with thioureas, thioamide, and thiobenzamide has offered a one-pot synthesis of 2-substituted 4-styrylthiazoles.Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.604815

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSES HETEROCYCLIQUES ET PROCEDES D'UTILISATION DE CEUX-CI
  申请人：MERCK & CO INC

  公开号：WO2001016121A1

  公开（公告）日：2001-03-08

  In accordance with the present invention, there are provided novel class of heterocyclic compounds and methods of use thereof. Compounds of the invention contain a substituted, unsaturated five, six or seven membered heterocyclic ring that includes at least one nitrogen atom and at least one carbon atom. At a ring position adjacent to a ring nitrogen atom, the heterocyclic ring has at least one substituent which includes a moiety, linked to the heterocyclic ring via an alkylene moiety, an alkynylene moiety or an azo group. Invention compounds are capable of a wide variety of uses including modulating physiological processes by functioning as agonists and antagonists of receptors in the nervous system, as insecticides, and as fungicides. The invention further provides methods of modulating the activity of excitatory amino acid receptors using a specifically defined class of heterocyclic compounds including the novel compounds referred to above. In one embodiment, there are provided methods of modulating metabotropic glutamate receptors. The present invention also discloses methods of treating disease using heterocyclic compounds. The invention further discloses methods of preventing disease conditions related to diseases of the pulmonary system, diseases of the nervous system, diseases of the cardiovascular system, diseases of the gastrointestinal system, diseases of the endocrine system, diseases of the exocrine system, diseases of the skin, cancer and diseases of the ophthalmic system. The invention also discloses pharmaceutically acceptable salt forms of the above-described heterocyclic compounds.

  根据本发明，提供了一类新型的杂环化合物及其使用方法。该发明的化合物包含一个取代的、不饱和的五、六或七元杂环环，其中至少包含一个氮原子和至少一个碳原子。在靠近环氮原子的环位置上，杂环环有至少一个取代基，包括一个官能团，通过烷基官能团、炔基官能团或偶氮基团连接到杂环环上。发明的化合物能够广泛应用，包括通过作为神经系统受体的激动剂和拮抗剂来调节生理过程，作为杀虫剂和杀菌剂。本发明还提供了使用特定定义的杂环化合物类来调节兴奋性氨基酸受体活性的方法，包括上述新型化合物。在一种实施例中，提供了调节代谢性谷氨酸受体的方法。本发明还揭示了使用杂环化合物治疗疾病的方法。本发明还揭示了预防与肺系统疾病、神经系统疾病、心血管系统疾病、胃肠系统疾病、内分泌系统疾病、外分泌系统疾病、皮肤疾病、癌症和眼科系统疾病相关的疾病状态的方法。本发明还揭示了上述杂环化合物的药物可接受的盐形式。
• Methods of modulating processes mediated by excitatory amino acid receptors
  申请人：Cosford Nicholas D. P.

  公开号：US06956049B1

  公开（公告）日：2005-10-18

  In accordance with the present invention, there are provided methods of modulating the activity of excitatory amino acid receptors using a specifically defined class of heterocyclic compounds. In one embodiment, there are provided methods of modulating metabotropic glutamate receptors. The present invention also discloses methods of treating disease using heterocyclic compounds. Diseases contemplated include cerebral ischemia, chronic neurodegeneration, psychiatric disorders, schizophrenia, mood disorders, emotion disorders, disorders of extrapyramidal motor function, obesity, disorders of respiration, motor control and function, attention deficit disorders, concentration disorders, pain disorders, neurodegenerative disorders, epilepsy, convulsive disorders, eating disorders, sleep disorders, sexual disorders, circadian disorders, drug withdrawal, drug addiction, compulsive disorders, anxiety, panic disorders, depressive disorders, skin disorders, retinal ischemia, retinal degeneration, glaucoma, disorders associated with organ transplantation, asthma, ischemia and astrocytomas. The invention further discloses methods of preventing disease conditions related to diseases of the pulmonary system, diseases of the nervous system, diseases of the cardiovascular system, diseases of the gastrointestinal system, diseases of the endocrine system, diseases of the exocrine system, diseases of the skin, cancer and diseases of the ophthalmic system. The invention also discloses pharmaceutically acceptable salt forms of heterocyclic compounds.

  根据本发明，提供了使用一类特定定义的杂环化合物来调节兴奋性氨基酸受体活性的方法。在一种实施例中，提供了调节代谢型谷氨酸受体的方法。本发明还揭示了使用杂环化合物治疗疾病的方法。所考虑的疾病包括脑缺血、慢性神经退行性疾病、精神障碍、精神分裂症、情绪障碍、运动功能外围疾病、肥胖症、呼吸、运动控制和功能障碍、注意力缺陷障碍、注意力障碍、疼痛障碍、神经退行性疾病、癫痫、惊厥性障碍、进食障碍、睡眠障碍、性障碍、昼夜节律障碍、药物戒断、药物成瘾、强迫障碍、焦虑、恐慌障碍、抑郁障碍、皮肤疾病、视网膜缺血、视网膜退化、青光眼、与器官移植相关的疾病、哮喘、缺血和星形细胞瘤。本发明还揭示了杂环化合物的药物可接受的盐形式的方法。
• Treatment of neuromuscular dysfunction of the lower urinary tract with selective mGlu5 antagonists
  申请人：Recordati S.A.

  公开号：US20040215284A1

  公开（公告）日：2004-10-28

  The invention is directed to methods of using antagonists selective for the metabotropic mGlu5 receptor to treat conditions of neuromuscular dysfunction of the lower urinary tract in a mammal. Provided are methods of treating a mammal suffering from a condition of neuromuscular dysfunction of the lower urinary tract by administering a selective mGlu5 antagonist. The selective mGlu5 antagonist may be administered alone or in combination with one or more additional therapeutic agent for treating such a condition. Also provided are methods of identifying selective mGlu5 antagonists that are useful for treating neuromuscular dysfunction of the lower urinary tract in a mammal.

  本发明涉及使用选择性代谢型mGlu5受体拮抗剂治疗哺乳动物下尿路神经肌肉功能障碍的方法。本发明提供了通过施用选择性 mGlu5 拮抗剂来治疗患有下尿路神经肌肉功能障碍的哺乳动物的方法。选择性 mGlu5 拮抗剂可单独给药或与一种或多种额外的治疗剂联合给药，以治疗这种病症。还提供了鉴定选择性mGlu5拮抗剂的方法，这些选择性mGlu5拮抗剂可用于治疗哺乳动物的下尿路神经肌肉功能障碍。
• 4-STYRYLTHIAZOLES. SYNTHESES AND RELATIONSHIPS AMONG ULTRAVIOLET ABSORPTION SPECTRA
  作者：PHILIP L. SOUTHWICK、DAVID I. SAPPER

  DOI：10.1021/jo01377a009

  日期：1954.12
• Sytsch; Smasnaja-Il'ina, Zhurnal Obshchei Khimii, 1963, vol. 33, p. 74,76, engl. Ausg. S. 68, 69
  作者：Sytsch、Smasnaja-Il'ina

  DOI：——

  日期：——