5-氨基-1-乙基-3-甲基-1H-吡唑-4-甲腈 | 102997-29-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-1-乙基-3-甲基-1H-吡唑-4-甲腈
• 英文名称: 1-ethyl-3-methyl-4-cyano-5-aminopyrazole
• 英文别名: 5-amino-4-cyano-1-ethyl-3-methylpyrazole；5-amino-4-cyano-3-methyl-1-ethyl-(1H)-pyrazole；5-Amino-1-ethyl-3-methyl-1H-pyrazole-4-carbonitrile；5-amino-1-ethyl-3-methylpyrazole-4-carbonitrile
• CAS: 102997-29-5
• 化学式: C₇H₁₀N₄
• 分子量: 150.183
• InChiKey: VSDBCFKGNFXCNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  5-氨基-1-乙基-3-甲基-1H-吡唑-4-甲腈 在 吡啶 、 sodium hydroxide 、 三氯化铝 、 硫酸 、 双氧水 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 68.0h， 生成 methyl 3-(1-ethyl-3-methyl-4-oxo-5H-pyrazolo[3,4-d]pyrimidin-6-yl)-4-propoxybenzoate
  参考文献：
  名称：

  一系列6-苯基吡唑并[3,4-d]嘧啶酮的合成及环GMP磷酸二酯酶的抑制活性。

  摘要：

  描述了一系列6-苯基吡唑并[3,4-d]嘧啶酮，它们是cGMP特异性（V型）磷酸二酯酶的特异性抑制剂。评价了酶和细胞活性以及体内口服降压活性。苯环的2位上的正丙氧基是活性所必需的。制备并评估了除2-正丙氧基外在5-位取代的一系列产物。这个职位可以容纳许多无关的团体。氨基衍生物非常有效，但缺乏代谢稳定性。碳连接的小杂环取代提供了高水平的活性和稳定性。细胞活性经常与体内活性相关。在这些化合物中，1,3-二甲基-6（2-丙氧基-5-甲磺酰胺基苯基）-1,5-二氢邻苯二酚[3，

  DOI：

  10.1021/jm950812j
• 作为产物：
  描述：

  5-amino-4-cyano-3-methyl-1-vinyl-(1H)-pyrazole 在 钯 作用下， 以 乙酸乙酯 为溶剂， 以76.7%的产率得到5-氨基-1-乙基-3-甲基-1H-吡唑-4-甲腈
  参考文献：
  名称：

  SULFONYLUREIDOPYRAZOLE DERIVATIVES

  摘要：

  公开了一种化学式（1）或（2）的磺酰脲吡唑衍生物。该衍生物对内皮素转化酶具有抑制活性，可用于治疗或预防各种心脏衰竭、气管收缩、神经紊乱、副分泌、血管紊乱、各种溃疡等疾病。

  公开号：

  EP0885890A1

文献信息

• Synthesis of 4-thiocarbamoyl-5-aminopyrazoles
  作者：P. Giori、A. C. Veronese、C. B. Vicentini、M. Guarneri

  DOI：10.1002/jhet.5570220434

  日期：1985.7

  Aryl and t-butylhydrazines react with 2-cyano-3-ethoxythiocrotonamide affording 2-cyano-3-aryl-t-butylhy-drazinothiocrotonamides. These intermediates can be easily cyclized to 4-thiocarbamoyl-5-aminopyrazoles by heating a few minutes in a strong base. Alkylhydrazines react with 2-cyano-3-ethoxythiocrotonamide yielding directly a mixture of the cyclized compounds 4-cyano-5-aminopyrazoles and 4-thio

  芳基和叔丁基肼与2-氰基-3-乙氧基硫代巴豆酰胺反应，得到2-氰基-3-芳基-叔丁基hy-drazinothiocrotonamides。通过在强碱中加热几分钟，这些中间体可以轻松地环化为4-硫代氨基甲酰基-5-氨基吡唑。烷基肼与2-氰基-3-乙氧基硫代巴豆酰胺反应，直接生成环化化合物4-氰基-5-氨基吡唑和4-硫代氨基甲酰基-5-氨基吡唑的混合物。
• Pyrazolopyrimidine Derivatives
  申请人：LABORATOIRES GLAXO SA

  公开号：EP0636626A1

  公开（公告）日：1995-02-01

  Pyrazolo[3,4-d]pyrimidin-4-one derivatives of formula (I) and salts and solvates thereof are described, in which: R¹ represents arylmethyl or C₁₋₆alkyl optionally substituted by one or more fluorine atoms; R² represents methyl; R³ represents C₂₋₄alkyl; R⁴ represents nitro, cyano, C₁₋₆alkoxy, C(=X)NR⁶R⁷, NR⁸R⁹, (CH₂)mNR¹⁰C(=Y)R¹¹ or a 5-membered heterocyclic ring selected from thienyl, thiazolyl and 1,2,4-triazolyl each ring optionally substituted by a C₁₋ ₄alkyl or aryl group; or when R¹ is arylmethyl or C₁₋₆alkyl substituted by one or more fluorine atoms then R⁴ may also represent hydrogen; R⁵ represents hydrogen or C₁₋₆alkyl; R⁶ represents hydrogen or C₁₋₆alkyl; R⁷ represents hydrogen, amino, hydroxyl, C₁₋₆alkyl, aryl or arylC₁₋₄alkyl; R⁸ represents hydrogen or C₁₋₆alkyl; R⁹ represents hydrogen, C₁₋₆alkyl, SO₂R¹², CO₂R¹², C(=NCN)SR¹² or C(=NCN)NR¹³R¹⁴; R¹⁰ represents hydrogen or C₁₋₆alkyl; R¹¹ represents C₁₋₆alkyl optionally substituted by one or more halogen atoms, or R¹¹ represents aryl, arylC₁₋₄alkyl, thienyl, NR¹⁵R¹⁶, CH₂NR¹⁷R¹⁸ or R¹⁰ and R¹¹ together represent -A(CH₂)n-; R¹² represents C₁₋₆alkyl, aryl or arylC₁₋₄alkyl; R¹³ represents hydrogen or C₁₋₆alkyl; R¹⁴ represents hydrogen, C₁₋₆alkyl, aryl, arylC₁₋₄alkyl or R¹³ and R¹⁴ together with the nitrogen atom to which they are attached form a morpholine, piperazine or N-C₁₋₄alkylpiperazine ring; R¹⁵ represents hydrogen or C₁₋₆alkyl or R¹⁰ and R¹⁵ together represent -A(CH₂)n-; R¹⁶ represents hydrogen, C₁₋₆alkyl, aryl, arylC₁₋₄alkyl, CO₂R¹², CH₂CO₂R¹² or R¹⁵ and R¹⁶ together with the nitrogen atom to which they are attached form a morpholine, piperazine or N-C₁₋₄alkylpiperazine ring; R¹⁷ represents hydrogen or C₁₋₆alkyl; R¹⁸ represents hydrogen, C₁₋₆alkyl, aryl, arylC₁₋₄alkyl, COR¹² or R¹⁷ and R¹⁸ together with the nitrogen atom to which they are attached form a morpholine, piperazine or N-C₁₋₄alkylpiperazine ring; A represents CH₂ or C=O; m represents zero or 1; n represents 1,2 or 3; X represents S or NH, or when R⁷ represents amino then X may also represent O; Y represents O or S; for use in therapy. These compounds are potent and selective inhibitors of cyclic guanosine 3',5'-monophosphate specific phosphodiesterase (cGMP specific PDE) and are useful in a variety of therapeutic areas, including the treatment of cardiovascular disorders.

  描述了式(I)的吡唑并[3,4-d]嘧啶-4-酮衍生物及其盐和溶剂化合物，其中：R¹代表芳基甲基或C₁₋₆烷基，可选择性地取代一个或多个氟原子；R²代表甲基；R³代表C₂₋₄烷基；R⁴代表硝基、氰基、C₁₋₆烷氧基、C(=X)NR⁶R⁷、NR⁸R⁹、(CH₂)mNR¹⁰C(=Y)R¹¹或选择自噻吩基、噻唑基和1,2,4-三唑基的5-成员杂环环，每个环可选择性地取代为C₁₋₄烷基或芳基；或当R¹为芳基甲基或C₁₋₆烷基取代一个或多个氟原子时，R⁴也可以代表氢；R⁵代表氢或C₁₋₆烷基；R⁶代表氢或C₁₋₆烷基；R⁷代表氢、氨基、羟基、C₁₋₆烷基、芳基或芳基C₁₋₄烷基；R⁸代表氢或C₁₋₆烷基；R⁹代表氢、C₁₋₆烷基、SO₂R¹²、CO₂R¹²、C(=NCN)SR¹²或C(=NCN)NR¹³R¹⁴；R¹⁰代表氢或C₁₋₆烷基；R¹¹代表C₁₋₆烷基，可选择性地取代一个或多个卤原子，或R¹¹代表芳基、芳基C₁₋₄烷基、噻吩基、NR¹⁵R¹⁶、CH₂NR¹⁷R¹⁸或R¹⁰和R¹¹一起代表-A(CH₂)n-；R¹²代表C₁₋₆烷基、芳基或芳基C₁₋₄烷基；R¹³代表氢或C₁₋₆烷基；R¹⁴代表氢、C₁₋₆烷基、芳基、芳基C₁₋₄烷基或R¹³和R¹⁴与它们连接的氮原子一起形成吗啡啉、哌嗪或N-C₁₋₄烷基哌嗪环；R¹⁵代表氢或C₁₋₆烷基或R¹⁰和R¹⁵一起代表-A(CH₂)n-；R¹⁶代表氢、C₁₋₆烷基、芳基、芳基C₁₋₄烷基、CO₂R¹²、CH₂CO₂R¹²或R¹⁵和R¹⁶与它们连接的氮原子一起形成吗啡啉、哌嗪或N-C₁₋₄烷基哌嗪环；R¹⁷代表氢或C₁₋₆烷基；R¹⁸代表氢、C₁₋₆烷基、芳基、芳基C₁₋₄烷基、COR¹²或R¹⁷和R¹⁸与它们连接的氮原子一起形成吗啡啉、哌嗪或N-C₁₋₄烷基哌嗪环；A代表CH₂或C=O；m代表零或1；n代表1,2或3；X代表S或NH，或当R⁷代表氨基时，X也可以代表O；Y代表O或S；用于治疗。这些化合物是环鸟苷3',5'-单磷酸特异性磷酸二酯酶（cGMP特异性PDE）的有效和选择性抑制剂，并在多种治疗领域中有用，包括治疗心血管疾病。
• GIORI, P.;VERONESE, A. C.;VICENTINI, C. B.;GUARNERI, M., J. HETEROCYCL. CHEM., 1985, 22, N 4, 1093-1096
  作者：GIORI, P.、VERONESE, A. C.、VICENTINI, C. B.、GUARNERI, M.

  DOI：——

  日期：——
• Synthesis and Cyclic GMP Phosphodiesterase Inhibitory Activity of a Series of 6-Phenylpyrazolo[3,4-<i>d</i>]pyrimidones
  作者：Bernard Dumaître、Nerina Dodic

  DOI：10.1021/jm950812j

  日期：1996.1.1

  A series of 6-phenylpyrazolo[3,4-d]pyrimidones is described which are specific inhibitors of cGMP specific (type V) phosphodiesterase. Enzymatic and cellular activity as well as in vivo oral antihypertensive activity are evaluated. A n-propoxy group at the 2-position of the phenyl ring is necessary for activity. A series of products substituted at the 5-position in addition to the 2-n-propoxy was prepared

  描述了一系列6-苯基吡唑并[3,4-d]嘧啶酮，它们是cGMP特异性（V型）磷酸二酯酶的特异性抑制剂。评价了酶和细胞活性以及体内口服降压活性。苯环的2位上的正丙氧基是活性所必需的。制备并评估了除2-正丙氧基外在5-位取代的一系列产物。这个职位可以容纳许多无关的团体。氨基衍生物非常有效，但缺乏代谢稳定性。碳连接的小杂环取代提供了高水平的活性和稳定性。细胞活性经常与体内活性相关。在这些化合物中，1,3-二甲基-6（2-丙氧基-5-甲磺酰胺基苯基）-1,5-二氢邻苯二酚[3，
• SULFONYLUREIDOPYRAZOLE DERIVATIVES
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0885890A1

  公开（公告）日：1998-12-23

  A sulfonylureidopyrazole derivative of formula (1) or (2) is disclosed. The derivative has an inhibitory activity on endothelin converting enzyme, and is useful for treating or preventing various cardiac failures, tracheal constrictions, nervous disorders, parasecretion, vascular disorders, various ulcers and the like.

  公开了一种化学式（1）或（2）的磺酰脲吡唑衍生物。该衍生物对内皮素转化酶具有抑制活性，可用于治疗或预防各种心脏衰竭、气管收缩、神经紊乱、副分泌、血管紊乱、各种溃疡等疾病。