3-tert-butyl-1-pentyl-1H-pyrazol-5-amine | 1217420-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-tert-butyl-1-pentyl-1H-pyrazol-5-amine
• 英文别名: 5-tert-butyl-2-pentylpyrazol-3-amine
• CAS: 1217420-78-4
• 化学式: C₁₂H₂₃N₃
• 分子量: 209.335
• InChiKey: RUSYDBDIOXWLEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-tert-butyl-1-pentyl-1H-pyrazol-5-amine 在 copper(l) iodide 、 lithium aluminium tetrahydride 、 亚硝酸特丁酯 、 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 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 13.0h， 生成 N-[(5-tert-butyl-2-pentylpyrazol-3-yl)methyl]-2-[3-fluoro-4-(methanesulfonamido)phenyl]propanamide
  参考文献：
  名称：

  Pyrazole C-region analogues of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists

  摘要：

  A series of 1-substituted 3-(t-butyl/trifluoromethyl)pyrazole C-region analogues of 2-(3-fluoro-4-methyl-sulfonamidophenyl) propanamides were investigated for hTRPV1 antagonism. The structure activity relationship indicated that the 3-chlorophenyl group at the 1-position of pyrazole was the optimized hydrophobic group for antagonistic potency and the activity was stereospecific to the S-configuration, providing exceptionally potent antagonists 13S and 16S with K-i(CAP) = 0.1 nM. Particularly significant, 13S exhibited antagonism selective for capsaicin and NADA and not for low pH or elevated temperature. Both compounds also proved to be very potent antagonists for rTRPV1, blocking in vivo the hypothermic action of capsaicin, consistent with their in vitro mechanism. The docking study of compounds 13S and 16S in our hTRPV1 homology model indicated that the binding modes differed somewhat, with that of 13S more closely resembling that of GRT12360. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.08.020
• 作为产物：
  描述：

  新戊酰基乙腈 、 pentylhydrazine hydrochloride 以 乙醇 、 水 为溶剂， 生成 3-tert-butyl-1-pentyl-1H-pyrazol-5-amine
  参考文献：
  名称：

  Pyrazole C-region analogues of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists

  摘要：

  A series of 1-substituted 3-(t-butyl/trifluoromethyl)pyrazole C-region analogues of 2-(3-fluoro-4-methyl-sulfonamidophenyl) propanamides were investigated for hTRPV1 antagonism. The structure activity relationship indicated that the 3-chlorophenyl group at the 1-position of pyrazole was the optimized hydrophobic group for antagonistic potency and the activity was stereospecific to the S-configuration, providing exceptionally potent antagonists 13S and 16S with K-i(CAP) = 0.1 nM. Particularly significant, 13S exhibited antagonism selective for capsaicin and NADA and not for low pH or elevated temperature. Both compounds also proved to be very potent antagonists for rTRPV1, blocking in vivo the hypothermic action of capsaicin, consistent with their in vitro mechanism. The docking study of compounds 13S and 16S in our hTRPV1 homology model indicated that the binding modes differed somewhat, with that of 13S more closely resembling that of GRT12360. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.08.020

文献信息

• NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
  申请人：Carroll William A.

  公开号：US20100069348A1

  公开（公告）日：2010-03-18

  Disclosed herein are cannabinoid receptor ligands of formula (I) wherein A 1 , A 5 , R x , X 4 , and z are as defined in the specification. Compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

  本文揭示了公式（I）中的大麻素受体配体，其中A1、A5、Rx、X4和z如规范中定义。还公开了包含这些化合物的组合物，以及使用这些化合物和组合物治疗疾病和疾病的方法。
• COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
  申请人：Wang Xueqing

  公开号：US20100249087A1

  公开（公告）日：2010-09-30

  Disclosed herein are cannabinoid receptor ligands of formula (I) wherein Ring A and R 1 are as defined in the specification. Compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and compositions are also described.

  本文披露了式(I)的大麻素受体配体，其中环A和R1如规范中所定义。还描述了包含这些化合物的组合物，以及使用这些化合物和组合物治疗疾病和疾病的方法。
• [EN] PROCESS FOR THE PREPARATION OF 8-(4-AMINOPHENOXY)-4H-PYRIDO[2,3-B]PYRAZIN-3-ONE DERIVATIVES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS DE 8-(4-AMINOPHÉNOXY)- 4H-PYRIDO[2,3-B]PYRAZIN-3-ONE
  申请人：CANCER REC TECH LTD

  公开号：WO2015075482A1

  公开（公告）日：2015-05-28

  The present invention pertains generally to the field of organic chemical synthesis, and in particular to certain methods for the synthesis of 8-(4-aminophenyoxy)- 4H-pyrido[2,3-b]pyrazin-3-one and related compounds (denoted herein as (3)) from 4-(4-aminophenyoxy)pyridine-2,3-diamine and related compounds (denoted herein as (1)), by reaction with glyoxylic acid (denoted herein as (2)). The compounds (3) are useful in the synthesis of known anti-cancer agents, such as 1-(5-tert-butyl-2-(4-methyl- phenyl)-pyrazol-3-yl)-3-[2-fluoro-4-[(3-oxo-4H-pyrido[2,3-b]pyrazin-8-yl)oxy]phenyl]urea.

  本发明一般涉及有机化学合成领域，特别是涉及从4-(4-氨基苯氧基)吡啶-2,3-二胺及相关化合物（以下简称为（1））与甘氧酸（以下简称为（2））反应，合成8-(4-氨基苯氧基)-4H-吡啶并[2,3-b]吡嗪-3-酮及相关化合物（以下简称为（3））的某些方法。这些化合物（3）在合成已知的抗癌药物中起到作用，例如1-(5-叔丁基-2-(4-甲基苯基)-吡唑-3-基)-3-[2-氟-4-[(3-氧代-4H-吡啶并[2,3-b]吡嗪-8-基)氧基]苯基]脲。
• Compounds as cannabinoid receptor ligands
  申请人：Abbott Laboratories

  公开号：US08288428B2

  公开（公告）日：2012-10-16

  Disclosed herein are cannabinoid receptor ligands of formula (I) wherein Ring A and R1 are as defined in the specification. Compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and compositions are also described.

  本文披露了式(I)的大麻素受体配体，其中环A和R1如规范中所定义。还描述了包含这些化合物的组合物以及使用这些化合物和组合物治疗病症和疾病的方法。
• Substituierte 1-Aryl-3-tert.-butyl-pyrazole
  申请人：BAYER AG

  公开号：EP0257479A1

  公开（公告）日：1988-03-02

  Es wurden neue 1-Aryl-3-tert.-butyl-pyrazole der allgemeinen Formel (I), bereitgestellt, in welcher R1 für Nitro oder Halogen steht, R2 für Halogen oder die Gruppierung -NR3R4 steht, sowie auch für Wasserstoff steht, wenn R1 Halogen bedeutet, wobei R3 für Wasserstoff, für jeweils gegebenenfalls substituiertes Alkyl, Alkenyl oder Alkinyl sowie für jeweils gegebenenfalls substituiertes Cycloalkyl oder Cycloalkylalkyl steht und R4 unabhängig von R3 für die gleichen Reste wie R3 steht, sowie zusätzlich für einen steht, wobei X für Sauerstoff oder Schwefel steht und R5 für Wasserstoff, Alkyl, Alkenyl, Alkinyl, Halogenalkyl, Alkoxyalkyl, Alkylthioalkyl, für gegebenenfalls substituiertes Cycloalkyl, für gegebenenfalls substituiertes Aryl, für Alkoxy, Alkylthio, für gegebenenfalls substituiertes Aryloxy, für gegebenenfalls substituiertes Arylthio, für Alkylamino, für Dialkylamino oder für gegebenenfalls substituiertes Arylamino steht; und Ar für gegebenenfalls substituiertes Phenyl, ausgenommen Dinitrophenyl, oder für gegebenenfalls substituiertes Pyridyl steht. Die neuen Verbindungen der Formel (I) besitzen stark ausgeprägte insektizide und akarizide Eigenschaften.

  通式(I)的新型 1-芳基-3-叔丁基吡唑、 其中 R1 是硝基或卤素、 R2 代表卤素或基团 -NR3R4，当 R1 为卤素时也代表氢，其中 R3 代表氢，在每种情况下代表任选取代的烷基、烯基或炔基，在每种情况下代表任选取代的环烷基或环烷基烷基，以及 R4 独立于 R3 代表与 R3 相同的基团，此外还代表 a 其中 X 代表氧或硫 R5 是氢、烷基、烯基、炔基、卤代烷基、烷氧基烷基、烷硫基烷基、任选取代的环烷基、任选取代的芳基、烷氧基、烷硫基、任选取代的芳氧基、任选取代的芳硫基、烷基氨基、二烷基氨基或任选取代的芳基氨基；以及 Ar 代表任选取代的苯基（不包括二硝基苯基）或任选取代的吡啶基。 式（I）的新化合物具有非常明显的杀虫和杀螨特性。