2-[(4-甲氧基苯基)氨基]-1,3-噻唑-4-羧酸 | 165682-75-7

• 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: 2-[(4-甲氧基苯基)氨基]-1,3-噻唑-4-羧酸
• 英文名称: 2-{[4-(methyloxy)phenyl]amino}-1,3-thiazole-4-carboxylic acid
• 英文别名: 2-(4-methoxyphenylamino)thiazole-4-carboxylic acid；2-[(4-methoxyphenyl)amino]-1,3-thiazole-4-carboxylic Acid；2-(4-methoxyanilino)-1,3-thiazole-4-carboxylic acid
• CAS: 165682-75-7
• 化学式: C₁₁H₁₀N₂O₃S
• mdl: MFCD04117341
• 分子量: 250.278
• InChiKey: FRHNAQQUMBLASW-UHFFFAOYSA-N

物化性质

• 沸点：
  466.7±51.0 °C(Predicted)
• 密度：
  1.432±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  99.7
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  N-(3-氨丙基)吗啉 、 2-[(4-甲氧基苯基)氨基]-1,3-噻唑-4-羧酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.17h， 以88%的产率得到N-(3-morpholinopropyl) 2-(4-methoxylphenylamino)thiazole-4-carboxamide
  参考文献：
  名称：

  在甲型流感病毒核蛋白三聚化过程中破坏保守的盐桥。

  摘要：

  流感感染中的抗病毒药物耐药性已成为对公共卫生的主要威胁。为了开发广谱的流感抑制剂来解决耐药性问题，我们之前确定了高度保守的核蛋白三聚体E339 ... R416盐桥为靶标，化合物1为通过EC50破坏盐桥的抑制剂甲型流感病毒= 2.7μM（A / WSN / 1933）。我们通过基于结构的方法进一步修饰了该化合物，并进行了抗病毒活性筛选，以鉴定化合物29和30的EC50值分别为110和120 nM，并且没有可测量的宿主细胞毒性。与临床使用的神经氨酸酶抑制剂相比，这两种化合物对耐药性A型流感病毒株和B型流感病毒显示出更好的活性，

  DOI：

  10.1021/acs.jmedchem.9b01244
• 作为产物：
  描述：

  乙基2-[(4-甲氧基苯基)氨基]-1,3-噻唑-4-羧酸酯 在 甲醇 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 2-[(4-甲氧基苯基)氨基]-1,3-噻唑-4-羧酸
  参考文献：
  名称：

  The discovery of potent blockers of the canonical transient receptor channels, TRPC3 and TRPC6, based on an anilino-thiazole pharmacophore

  摘要：

  Lead optimization of piperidine amide HTS hits, based on an anilino-thiazole core, led to the identification of analogs which displayed low nanomolar blocking activity at the canonical transient receptor channels 3 and 6 (TRPC3 & 6) based on FLIPR (carbachol stimulated) and electrophysiology (OAG stimulated) assays. In addition, the anilino-thiazole amides displayed good selectivity over other TRP channels (TRPA1, TRPV1, and TRPV4), as well as against cardiac ion channels (CaV1.2, hERG, and NaV1.5). The high oxidation potential of the aliphatic piperidine and aniline groups, as well as the lability of the thiazole amide group contributed to the high clearance observed for this class of compounds. Conversion of an isoquinoline amide to a naphthyridine amide markedly reduced clearance for the bicyclic piperidines, and improved oral bioavailability for this compound series, however TRPC3 and TRPC6 blocking activity was reduced substantially. Although the most potent anilino-thiazole amides ultimately lacked oral exposure in rodents and were not suitable for chronic dosing, analogs such as 14-19, 22, and 23 are potentially valuable in vitro tool compounds for investigating the role of TRPC3 and TRPC6 in cardiovascular disease. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.06.047

文献信息

• SUBSTITUTED THIAZOL-2-YLAMINE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE AS 11-BETA HSD1 MODULATORS
  申请人：Polisetti Dharma Rao

  公开号：US20120029029A1

  公开（公告）日：2012-02-02

  The present invention is directed to substituted thiazol-2-ylamine derivatives and pharmaceutically acceptable salts thereof that inhibit 11βHSD1 and that may be useful in the treatment of diseases in which modulation or inhibition of 11βHSD1 is beneficial or where a reduction in intracellular glucorticoid levels is desirable. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases, disorders, or conditions in which modulation or inhibition of 11βHSD1 is beneficial or where a reduction in intracellular glucorticoid levels is desirable.

  本发明涉及取代噻唑-2-基胺衍生物及其药学上可接受的盐，其抑制11βHSD1并可能有助于治疗调节或抑制11βHSD1有益或需要降低细胞内糖皮质激素水平的疾病。本发明还涉及包含这些化合物的制药组合物以及在治疗调节或抑制11βHSD1有益或需要降低细胞内糖皮质激素水平的疾病、疾病或病况中使用这些化合物和组合物的用途。
• Substituted thiazol-2-ylamine derivatives, pharmaceutical compositions, and methods of use as 11-beta HSD1 modulators
  申请人：Polisetti Dharma Rao

  公开号：US08513430B2

  公开（公告）日：2013-08-20

  The present invention is directed to substituted thiazol-2-ylamine derivatives and pharmaceutically acceptable salts thereof that inhibit 11βHSD1 and that may be useful in the treatment of diseases in which modulation or inhibition of 11βHSD1 is beneficial or where a reduction in intracellular glucorticoid levels is desirable. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases, disorders, or conditions in which modulation or inhibition of 11βHSD1 is beneficial or where a reduction in intracellular glucorticoid levels is desirable.

  本发明涉及取代噻唑-2-胺衍生物及其药学上可接受的盐，其抑制11βHSD1并可用于治疗调节或抑制11βHSD1有益或需要降低细胞内糖皮质激素水平的疾病。本发明还涉及包括这些化合物的制药组合物以及在治疗调节或抑制11βHSD1有益或需要降低细胞内糖皮质激素水平的这些疾病、疾病或病状中使用这些化合物和组合物的用途。
• US8513430B2
  申请人：——

  公开号：US8513430B2

  公开（公告）日：2013-08-20
• [EN] SUBSTITUTED THIAZOL-2-YLAMINE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE AS 11-BETA HSD1 MODULATORS<br/>[FR] DÉRIVÉS DE THIAZOL-2-YLAMINE SUBSTITUÉS, COMPOSITIONS PHARMACEUTIQUES ET PROCÉDÉS D'UTILISATION EN TANT QUE MODULATEURS DE 11-BÊTA-HSD1
  申请人：HIGH POINT PHARMACEUTICALS LLC

  公开号：WO2012015715A1

  公开（公告）日：2012-02-02

  The present invention is directed to substituted thiazol-2-ylamine derivatives and pharmaceutically acceptable salts thereof that inhibit 11βHSD1 and that may be useful in the treatment of diseases in which modulation or inhibition of 11βHSD1 is beneficial or where a reduction in intracellular glucorticoid levels is desirable. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases, disorders, or conditions in which modulation or inhibition of 11βHSD1 is beneficial or where a reduction in intracellular glucorticoid levels is desirable.
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2012037349A2

  公开（公告）日：2012-03-22

  Compounds, pharmaceutical compositions containing them, and their use treatment of conditions mediated by the TRPC3 and/or TRPC6 ion channels.