4-(5-甲硫基-2H-1,2,4-三唑-3-基)吡啶 | 3770-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-(5-甲硫基-2H-1,2,4-三唑-3-基)吡啶
• 英文名称: 4-(5-methylsulfanyl-1H-[1,2,4]triazol-3-yl)-pyridine
• 英文别名: 4-(5-Methylmercapto-1H-[1,2,4]triazol-3-yl)-pyridin；4-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)pyridine
• CAS: 3770-47-6
• 化学式: C₈H₈N₄S
• mdl: MFCD01691595
• 分子量: 192.244
• InChiKey: XSWFUYNRLMZIRB-UHFFFAOYSA-N

物化性质

• 熔点：
  165-166 °C(Solv: ethanol (64-17-5))
• 沸点：
  450.0±47.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5-甲硫基-2H-1,2,4-三唑-3-基)吡啶 在 potassium permanganate 、 双氧水 、 溶剂黄146 作用下， 生成 4-(5-methanesulfonyl-1H-[1,2,4]triazol-3-yl)-pyridine
  参考文献：
  名称：

  Yoshida; Asai, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 951

  摘要：

  DOI：
• 作为产物：
  描述：

  1-异烟酰(硫代氨基甲酰肼) 在 sodium hydroxide 、 sodium ethanolate 作用下， 生成 4-(5-甲硫基-2H-1,2,4-三唑-3-基)吡啶
  参考文献：
  名称：

  Yoshida; Asai, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 951

  摘要：

  DOI：

文献信息

• Compositions and methods for inhibiting TGF-beta
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20040157861A1

  公开（公告）日：2004-08-12

  This invention provides compounds that are inhibitors of the TGF-&bgr; signaling pathway. The compounds are represented by formula I: 1 where A′ is N or CH; Ring B is preferably an triazolyl, imidazolyl, or thiazolyl ring; —X-D- is a linker group; and G is an optionally substituted aryl or heteroaryl ring. The compounds are useful for treating cardiovascular disease.

  该发明提供了一些抑制TGF-&bgr;信号通路的化合物。这些化合物由公式I表示：其中A'是N或CH；环B最好是三唑基、咪唑基或噻唑基环；—X-D-是连接基团；G是可选的取代芳基或杂环基。这些化合物可用于治疗心血管疾病。
• Substituted 1-(4-aminophenly)triazoles and their use as anti-inflammatory agents
  申请人：Boehringer Ingelheim Pharmaceuticals, Inc.

  公开号：US06451820B1

  公开（公告）日：2002-09-17

  Compounds of formula I wherein: R1 is pyridyl optionally substituted with halogen, C1-4 alkyl, C1-4 alkenyl, CN, Me2N, CO2Me, OMe, aryl, heterocyclyl, or R4; R2 is CF3; halogen; CN; branched or unbranched C1-8 alkyl; branched or unbranched C1-8 alkenyl; C3-8 cycloalkyl optionally substituted with OH, CN, or methoxy; C1-8 alkoxy; C1-4 alkyloxyalkyl; C1-8 alkylthio; C1-4 alkylthioalkyl; C1-8 dialkylamino; C1-4 dialkylaminoalkyl; CO2R4; or aryl connected to the triazole in any position that makes a stable bond and wherein the aryl thereof is optionally substituted with halogen, C1-4 alkyl, C1-4 alkenyl, CN, Me2N, CO2Me, OMe, aryl, heterocyclyl, or R4; L is —NHC(O)—; —NHC(O)O—; —NHC(O)C(O)—; —NHC(S)—; —NH—; —NHC(O)NH—; —NHC(S)NH—; —NHCH2—; —NHCH(R5)—, wherein R5 is H, CN, C1-6 alkyl, C1-6 alkyloxyalkyl, C1-6 alkylthioalkyl, C1-6 alkylsulfinylalkyl, C1-6 alkylsulfonylalkyl, C3-6 cycloalkyl, heterocyclyl, or aryl optionally substituted with a halogen, C1-4 alkyl, CN, Me2N, CO2Me, or OMe; R3 is C1-8 alkyl; C1-8 alkyloxy; C1-8 alkylthio; C1-8 alkylamino; C1-4 alkoxyalkyl; C1-4 alkylthioalkyl; C1-4 alkylaminoalkyl; C1-4 dialkylalkylaminoalkyl; —CO2R6; —N(R6)2; —NH(R6); —C(O)R6; —OR6; S(O)nR6 wherein n is 0, 1, or 2; —SO2NHR6; —SO2N(R6)2; or carbocyclyl or heterocyclyl, wherein the carbocyclyl or heterocyclyl thereof is optionally substituted with one or more of the following: halogen, —CN, —NO2, —SO2NH2, or R6, wherein R6 is phenyl, heterocyclyl, C3-6 cycloalkyl, C1-6 alkyl, C2-6 alkenyl, C1-6 alkyloxyalkyl, C1-6 alkylthioalkyl, C1-6 alkyl-sulfinylalkyl, C1-6 alkylsulfonylalkyl, or C2-6 alkynyl, and R6 is optionally substituted with halogen, —OH, alkyloxy, —CN, —COO-lower alkyl, —CONH-lower alkyl, —CON(lower alkyl)2, dialkylamino, phenyl, or heterocyclyl; and R4 is C1-4 alkyl or C1-4 alkenyl optionally substituted with carbocyclyl or heterocyclyl, or a pharmaceutically acceptable derivative thereof, pharmaceutical compositions comprising compounds of formula I, and methods of treating an inflammatory disease using compounds of formula I.

  化合物的化学式I，其中： R1是吡啶基，可选地被卤素，C1-4烷基，C1-4烯基，CN，Me2N，CO2Me，OMe，芳基，杂环基或R4取代； R2是CF3，卤素，CN，支链或非支链C1-8烷基，支链或非支链C1-8烯基，C3-8环烷基，可选地被OH，CN或甲氧基取代；C1-8烷氧基；C1-4烷氧基烷基；C1-8烷基硫醚；C1-4烷硫醚烷基；C1-8二烷基氨基；C1-4二烷基氨基烷基；CO2R4；或连接到三唑环的芳基，在其中使稳定键，并且其中的芳基可选地被卤素，C1-4烷基，C1-4烯基，CN，Me2N，CO2Me，OMe，芳基，杂环基或R4取代； L是-NHC（O）-；-NHC（O）O-；-NHC（O）C（O）-；-NHC（S）-；-NH-；-NHC（O）NH-；-NHC（S）NH-；-NHCH2-；-NHCH（R5）-，其中R5是H，CN，C1-6烷基，C1-6烷氧基烷基，C1-6烷基硫醚烷基，C1-6烷基亚砜基烷基，C1-6烷基磺酰基烷基，C3-6环烷基，杂环基或芳基，可选地被卤素，C1-4烷基，CN，Me2N，CO2Me或OMe取代； R3是C1-8烷基；C1-8烷氧基；C1-8烷基硫醚；C1-8烷基氨基；C1-4烷氧基烷基；C1-4烷硫醚烷基；C1-4烷基氨基烷基；C1-4二烷基烷基氨基烷基；-CO2R6；-N（R6）2；-NH（R6）；-C（O）R6；-OR6；S（O）nR6，其中n为0，1或2；-SO2NHR6；-SO2N（R6）2；或碳环烷基或杂环基，其中碳环烷基或杂环基可选地被以下一种或多种取代：卤素，-CN，-NO2，-SO2NH2或R6，其中R6是苯基，杂环基，C3-6环烷基，C1-6烷基，C2-6烯基，C1-6烷氧基烷基，C1-6烷硫醚烷基，C1-6烷基亚砜基烷基，C1-6烷基磺酰基烷基或C2-6炔基，并且R6可选地被卤素，-OH，烷氧基，-CN，-COO-较低烷基，-CONH-较低烷基，-CON（较低烷基）2，二烷基氨基，苯基或杂环基取代； R4是C1-4烷基或C1-4烯基，可选地被碳环烷基或杂环基取代，或其药学上可接受的衍生物，包括化合物I的制药组合物以及使用化合物I治疗炎症性疾病的方法。
• Compositions and method for inhibiting TGF-β
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US07361669B2

  公开（公告）日：2008-04-22

  This invention provides compounds that are inhibitors of the TGF-β signaling pathway. The compounds are represented by formula I: where A′ is N or CH; Ring B is preferably an triazolyl, imidazolyl, or thiazolyl ring; —X-D- is a linker group; and G is an optionally substituted aryl or heteroaryl ring. The compounds are useful for treating cardiovascular disease.

  本发明提供了抑制TGF-β信号通路的化合物。这些化合物由公式I表示：其中A'是N或CH；环B最好是三唑基、咪唑基或噻唑基环；-X-D-是一个连接基团；而G是一个可选的取代芳基或杂环基。这些化合物可用于治疗心血管疾病。
• 3-Aryl-5-alkylthio-4H-1,2,4-triazoles
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0276793B1

  公开（公告）日：1993-06-16
• COMPOSITIONS AND METHODS FOR INHIBITING TGF-&bgr;
  申请人：MILLENNIUM PHARMACEUTICALS, INC.

  公开号：EP1581222A2

  公开（公告）日：2005-10-05