3-氨基-4-(4-甲基苯基)噻吩-2-羧酸甲酯 | 160133-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 3-氨基-4-(4-甲基苯基)噻吩-2-羧酸甲酯
• 英文名称: methyl 3-amino-4-(4-toluyl)-2-thiophenecarboxylate
• 英文别名: methyl 3-amino-4-(p-tolyl)thiophene-2-carboxylate；methyl 3-amino-4-(4-methylphenyl)thiophene-2-carboxylate
• CAS: 160133-75-5
• 化学式: C₁₃H₁₃NO₂S
• mdl: MFCD04116501
• 分子量: 247.318
• InChiKey: UJJDUVOANRRUHL-UHFFFAOYSA-N

物化性质

• 沸点：
  391.5±42.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-氨基-4-(4-甲基苯基)噻吩-2-羧酸甲酯 在 ammonium sulfate 、 氨 、 四氯化锡 作用下， 以 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 71.5h， 生成 1-(1-hydroxyethoxymethyl)-7-phenylthieno<3,2-d>pyrimidine-2,4-dione
  参考文献：
  名称：

  噻吩并[3,2 - d ]嘧啶-2,4-二酮环状和无环核苷的合成作为潜在的抗HIV药物

  摘要：

  按照Vorbrüggen和Niedballa的方法[7]，通过7-甲基或芳基噻吩并[3,2 - d ]-嘧啶-2,4-二酮的烷基化反应，可以合成环状和无环核苷。可能的脱保护后，获得了潜在的抗HIV药物。

  DOI：

  10.1002/jhet.5570310208
• 作为产物：
  描述：

  对甲基苯乙腈 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 3-氨基-4-(4-甲基苯基)噻吩-2-羧酸甲酯
  参考文献：
  名称：

  噻吩并[3,2 - d ]嘧啶-2,4-二酮环状和无环核苷的合成作为潜在的抗HIV药物

  摘要：

  按照Vorbrüggen和Niedballa的方法[7]，通过7-甲基或芳基噻吩并[3,2 - d ]-嘧啶-2,4-二酮的烷基化反应，可以合成环状和无环核苷。可能的脱保护后，获得了潜在的抗HIV药物。

  DOI：

  10.1002/jhet.5570310208

文献信息

• THIENOPYRIMIDINONE DERIVATIVES AS mGluR1 ANTAGONISTS
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US20140228565A1

  公开（公告）日：2014-08-14

  Disclosed are thienopyrimidinone derivatives as antagonists that act on metabotropic glutamate receptor subtype 1. The thienopyrimidinone derivatives show pharmacological activity against metabotropic glutamate receptor-related diseases, including pain, such as neuropathic pain and migraine, psychiatric diseases, such as anxiety disorder and schizophrenia, urinary incontinence, and neurodegenerative diseases, such as Parkinson's disease and Alzheimer's disease. Also disclosed are methods for preparing the thienopyrimidinone derivatives, and pharmaceutical compositions containing the thienopyrimidinone derivatives as active ingredients.

  披露了作为对代谢型谷氨酸受体亚型1起作用的拮抗剂的噻吩嘧啶酮衍生物。这些噻吩嘧啶酮衍生物显示出对代谢型谷氨酸受体相关疾病的药理活性，包括疼痛，如神经病性疼痛和偏头痛，精神疾病，如焦虑症和精神分裂症，尿失禁，以及神经退行性疾病，如帕金森病和阿尔茨海默病。还披露了制备这些噻吩嘧啶酮衍生物的方法，以及含有这些噻吩嘧啶酮衍生物作为活性成分的药物组合物。
• Thienopyrimidinone derivatives as mGluR1 antagonists
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US09260448B2

  公开（公告）日：2016-02-16

  Disclosed are thienopyrimidinone derivatives as antagonists that act on metabotropic glutamate receptor subtype 1. The thienopyrimidinone derivatives show pharmacological activity against metabotropic glutamate receptor-related diseases, including pain, such as neuropathic pain and migraine, psychiatric diseases, such as anxiety disorder and schizophrenia, urinary incontinence, and neurodegenerative diseases, such as Parkinson's disease and Alzheimer's disease. Also disclosed are methods for preparing the thienopyrimidinone derivatives, and pharmaceutical compositions containing the thienopyrimidinone derivatives as active ingredients.

  本发明涉及噻唑嘧啶酮衍生物，作为代谢型谷氨酸受体亚型1的拮抗剂。该噻唑嘧啶酮衍生物对代谢型谷氨酸受体相关疾病具有药理活性，包括疼痛，如神经病性疼痛和偏头痛，精神疾病，如焦虑症和精神分裂症，尿失禁以及神经退行性疾病，如帕金森病和阿尔茨海默病。本发明还涉及制备噻唑嘧啶酮衍生物的方法，以及含有该噻唑嘧啶酮衍生物作为活性成分的药物组合物。
• Novel thienopyrimidinones as mGluR1 antagonists
  作者：Youngjae Kim、Jeeyeon Kim、Sora Kim、Yooran Ki、Seon Hee Seo、Jinsung Tae、Min Kyung Ko、Hyun-Seo Jang、Eun Jeong Lim、Chiman Song、YoonJeong Cho、Hae-Young Koh、Youhoon Chong、Il Han Choo、Gyochang Keum、Sun-Joon Min、Hyunah Choo

  DOI：10.1016/j.ejmech.2014.08.027

  日期：2014.10

  There has been much attention to discover mGluR1 antagonists for treating various central nervous system diseases such as seizures and neuropathic pain. Thienopyrimidinone derivatives were designed, synthesized, and biologically evaluated against mGluR1. Among the synthesized compounds, 3-(4-methoxyphenyl)-7-(o-tolyl)thienopyrimidin-4-one 30 exhibited the most potent inhibitory activity with an IC50 value of 45 nM and good selectivity over mGluR5. Also, the selective mGluR1 antagonist 30 showed marginal hERG channel activity (IC50 = 9.87 mu M), good profiles to CYP isozymes, and a good pharmacokinetic profile. Overall, the compound 30 was identified as a selective mGluR1 antagonist with a good pharmacokinetic profile, which is probably devoid of cardiac side effect and drug drug interactions. Therefore, the compound 30 can be expected to be broadly used as mGluR1 antagonistic chemical probe in in vitro and in vivo study for investigating CNS diseases. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Discovery of new thienopyrimidinone derivatives displaying antimalarial properties toward both erythrocytic and hepatic stages of Plasmodium
  作者：Anita Cohen、Peggy Suzanne、Jean-Charles Lancelot、Pierre Verhaeghe、Aurélien Lesnard、Louise Basmaciyan、Sébastien Hutter、Michèle Laget、Aurélien Dumètre、Lucie Paloque、Eric Deharo、Maxime D. Crozet、Pascal Rathelot、Patrick Dallemagne、Audrey Lorthiois、Carol Hopkins Sibley、Patrice Vanelle、Alexis Valentin、Dominique Mazier、Sylvain Rault、Nadine Azas

  DOI：10.1016/j.ejmech.2015.03.011

  日期：2015.5

  A preliminary in vitro screening of compounds belonging to various chemical families from our library revealed the thieno[3,2-d]pyrimidin-4(3H)-one scaffold displayed a promising profile against Plasmodium falciparum. Then, 120 new derivatives were synthesized and evaluated in vitro; compared to drug references, 40 showed good activity toward chloroquine sensitive (IC50 35-344 nM) and resistant (IC50 45-800 nM) P. falciparum strains. They were neither cytotoxic (CC50 15-50 mu M) toward HepG2 and CHO cells, nor mutagenic. Structure activity relationships were defined. The lead-compound also appeared active against the Plasmodium liver stages (Plasmodium yoelii IC50 = 35 nM) and a preliminary in vivo evaluation indicated the in vitro activity was preserved (45% reduction in parasitemia compared to untreated infected mice). A mechanistic study demonstrated these molecules do not involve any of the pathways described for commercial drugs and exert a specific activity on the ring and trophozoite stages. 2015 Elsevier Masson SAS. All rights reserved.
• US9260448B2
  申请人：——

  公开号：US9260448B2

  公开（公告）日：2016-02-16