1-(3-甲基苯基)三唑-4-羧酸 | 944901-55-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(3-甲基苯基)三唑-4-羧酸
• 英文名称: 1-(m-tolyl)-1H-1,2,3-triazole-4-carboxylic acid
• 英文别名: 1-(3-methylphenyl)-1H-1,2,3-triazole-4-carboxylic acid；1-(3-methylphenyl)triazole-4-carboxylic acid
• CAS: 944901-55-7
• 化学式: C₁₀H₉N₃O₂
• mdl: MFCD10696376
• 分子量: 203.2
• InChiKey: SLGDDWABRNAGHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-甲基苯基)三唑-4-羧酸 在 potassium pyrosulfate 、 silver(l) oxide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 1-(m-tolyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  炔丙醇一锅法合成1-单取代1,2,3-三唑

  摘要：

  实现了由炔丙醇和各种芳基叠氮化物一锅法合成 1-单取代-1,2,3-三唑。这种简单的方法通过三步一锅法以良好到极好的收率提供了对各种 1-单取代 1,2,3-三唑衍生物的简洁有效的访问。

  DOI：

  10.1055/s-0036-1589157
• 作为产物：
  描述：

  1-azido-3-methylbenzene 在 potassium permanganate 、 copper(l) iodide 、 sodium carbonate 、 sodium ascorbate 作用下， 以 乙腈 为溶剂， 反应 13.0h， 生成 1-(3-甲基苯基)三唑-4-羧酸
  参考文献：
  名称：

  炔丙醇一锅法合成1-单取代1,2,3-三唑

  摘要：

  实现了由炔丙醇和各种芳基叠氮化物一锅法合成 1-单取代-1,2,3-三唑。这种简单的方法通过三步一锅法以良好到极好的收率提供了对各种 1-单取代 1,2,3-三唑衍生物的简洁有效的访问。

  DOI：

  10.1055/s-0036-1589157

文献信息

• Highly regioselective and sustainable solar click reaction: a new post-synthetic modified triazole organic polymer as a recyclable photocatalyst for regioselective azide–alkyne cycloaddition reaction
  作者：Dolly Yadav、Nem Singh、Tae Wu Kim、Jae Young Kim、No-Joong Park、Jin-Ook Baeg

  DOI：10.1039/c9gc00894b

  日期：——

  and regioselectivity. The reaction was studied for a series of substrates and the absolute regioselectivity of a representative triazole product has also been confirmed by X-ray crystallography. The proficiency and chemical orthogonality of the Ni-TLOP are remarkable and it shows enhanced efficiency and regioselectivity. The use of a recyclable photocatalyst and non-hazardous reagents makes the catalytic

  在寻找独特而有效的催化剂以使该过程高效，绿色和可持续的过程中，对药用活性1,2,3-三唑的合成一直进行了严格的审查。在这里，我们提出了一种新的可见光活性镍（II）Cyclam集成的三唑连接的有机聚合物（Ni-TLOP）光催化剂，具有出色的效率和区域选择性，可合成1,2,3-三唑化合物。研究了一系列底物的反应，并且还通过X射线晶体学证实了代表性三唑产物的绝对区域选择性。Ni-TLOP的熟练度和化学正交性非常出色，并且显示出更高的效率和区域选择性。可循环使用的光催化剂和非危险试剂的使用使催化系统具有可持续性和环境友好性。这种光催化的点击反应技术已成功应用于最畅销的抗癫痫药rufinamide的合成。
• NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE
  申请人：Bischoff Alexander

  公开号：US20100160323A1

  公开（公告）日：2010-06-24

  The present invention relates to piperazine derivatives that act as inhibitors of stearoyl-CoA desaturase. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.

  本发明涉及作为硬脂酰辅酶A去饱和酶抑制剂的哌嗪衍生物。该发明还涉及制备这些化合物的方法、含有这些化合物的组合物，以及使用这些化合物进行治疗的方法。
• METHODS FOR THE TREATMENT OF NEUROLOGICAL DISORDERS
  申请人：Yumanity Therapeutics

  公开号：US20180193325A1

  公开（公告）日：2018-07-12

  The present disclosure provides compounds and methods useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.

  本公开提供了在治疗神经系统疾病方面有用的化合物和方法。本发明的化合物可以单独或与其他药用活性剂结合使用，用于治疗或预防神经系统疾病。
• TRIAZOLE CARBOXAMIDES AND USES THEREOF
  申请人：Hoffman-La Roche Inc.

  公开号：US20150191458A1

  公开（公告）日：2015-07-09

  The invention relates to compounds of formula wherein R 1 is phenyl or pyridinyl, optionally substituted by halogen, lower alkyl, lower alkoxy, lower alkyl substituted by halogen and lower alkoxy substituted by halogen; X 1 is —N═ or CH; X 2 is CR 2 or ═N—; X 3 is —N═ or CH; with the proviso that only two of X 1 , X 2 or X 3 are nitrogen; wherein is a triazole group, selected from R 2 is hydrogen or lower alkyl; Z is a bond, —O— or —CH 2 —; or to pharmaceutically suitable acid addition salts thereof It has now been found that the compounds of formulas I have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The compounds may be used for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  该发明涉及以下式化合物： 其中 R1是苯基或吡啶基，可选择地被卤素，较低烷基，较低烷氧基，被卤素取代的较低烷基和被卤素取代的较低烷氧基取代； X1是—N═或CH； X2是CR2或═N—； X3是—N═或CH； 但仅有两个X1、X2或X3是氮； 其中 n是三唑基团，选择自 R2是氢或较低烷基； Z是键，—O—或—CH2—； 或其药学上适宜的酸盐 现已发现，上述式I的化合物具有良好的亲和力与痕量胺相关受体（TAARs）结合，尤其是与TAAR1结合。 这些化合物可用于治疗抑郁症、焦虑症、双相情感障碍、注意缺陷多动障碍（ADHD）、与压力相关的障碍、如精神分裂症，神经系统疾病如帕金森病，神经退行性疾病如阿尔茨海默病，癫痫，偏头痛，高血压，物质滥用和代谢性疾病，如进食障碍，糖尿病，糖尿病并发症，肥胖，血脂异常，能量消耗和吸收障碍，体温稳态障碍，睡眠和昼夜节律障碍，以及心血管疾病。
• [EN] TRIAZOLE CARBOXAMIDE DERIVATIVES<br/>[FR] DÉRIVÉS TRIAZOLE CARBOXAMIDE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014041106A1

  公开（公告）日：2014-03-20

  The invention relates to compounds of formula (I), wherein R1 is phenyl or pyridinyl, optionally substituted by halogen, lower alkyl, lower alkoxy, lower alkyl substituted by halogen and lower alkoxy substituted by halogen; X1 is -N= or CH; X2 is CR2 or =N-; X3 is -N= or CH; with the proviso that only two of X1, X2 or X3 are nitrogen; wherein is a triazole group, selected from R2 is hydrogen or lower alkyl; Z is a bond, -O- or -CH2-; or to pharmaceutically suitable acid addition salts thereof. It has now been found that the compounds of formulas I have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The compounds may be used for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  该发明涉及以下化合物的结构（I），其中R1是苯基或吡啶基，可以选择性地被卤素、低烷基、低烷氧基、被卤素取代的低烷基和被卤素取代的低烷氧基取代；X1是-N=或CH；X2是CR2或=N-；X3是-N=或CH；但须注意X1、X2或X3中只有两个是氮；其中是三唑基团，选择自R2是氢或低烷基；Z是键，-O-或-CH2-；或其药学上适宜的酸盐。现已发现，公式I的化合物对痕量胺相关受体（TAARs）具有良好的亲和力，特别是对TAAR1。这些化合物可用于治疗抑郁症、焦虑症、躁郁症、注意力缺陷多动障碍（ADHD）、与压力有关的障碍、精神分裂症等精神障碍、帕金森病等神经疾病、阿尔茨海默病等神经退行性疾病、癫痫、偏头痛、高血压、物质滥用以及代谢紊乱，如进食障碍、糖尿病、糖尿病并发症、肥胖症、血脂异常、能量消耗和吸收障碍、体温稳态障碍、睡眠和昼夜节律障碍以及心血管疾病。