4-{[(1-propyl-1H-imidazol-5-yl)methyl]thio}phenylamine | 597583-17-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-{[(1-propyl-1H-imidazol-5-yl)methyl]thio}phenylamine
• 英文别名: 4-[(3-Propylimidazol-4-yl)methylsulfanyl]aniline
• CAS: 597583-17-0
• 化学式: C₁₃H₁₇N₃S
• mdl: MFCD23194133
• 分子量: 247.364
• InChiKey: OKXDTLMVLPTTRZ-UHFFFAOYSA-N

物化性质

• 熔点：
  49-51 °C
• 沸点：
  483.9±30.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-{[(1-propyl-1H-imidazol-5-yl)methyl]thio}phenylamine 在 盐酸 作用下， 以 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 106.5h， 生成 4-[(S)-(1-丙基-1H-咪唑-5-基)甲亚磺酰基]苯胺
  参考文献：
  名称：

  BIPHENYL COMPOUND AS CCR2/CCR5 RECEPTOR ANTAGONIST

  摘要：

  公开号：

  EP3567028B1
• 作为产物：
  描述：

  (1-propyl-2-sulfanyl-1H-imidazol-5-yl)methanol 在 氯化亚砜 、 双氧水 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 异丙醇 、 正丁醇 为溶剂， 反应 32.5h， 生成 4-{[(1-propyl-1H-imidazol-5-yl)methyl]thio}phenylamine
  参考文献：
  名称：

  BIPHENYL COMPOUND AS CCR2/CCR5 RECEPTOR ANTAGONIST

  摘要：

  公开号：

  EP3567028B1

文献信息

• PROCESS FOR PRODUCING OPTICALLY ACTIVE SULFOXIDE DERIVATIVE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1484322A1

  公开（公告）日：2004-12-08

  A process for preparing an optically active sulfoxide derivative (I) having CCR5 antagonism without causing side reactions such as racemization and Pummerer rearrangement, which comprises reacting a compound (II) with a compound (III) as shown by the following scheme: wherein R1 represents hydrogen, an aliphatic hydrocarbon group or an aromatic group; R2 represents halogeno, alkyl, hydroxyl, amino, an aromatic group, etc.; R3 represents a 5- or 6-membered ring; R4 represents hydrogen, alkyl, alkoxy or halogeno; R5 represents hydrogen, a hydrocarbon group, a heterocyclic group, acyl, etc.; ring A represents an optionally substituted benzene ring; X represents a bond or divalent group comprising a linear part constituted of 1 to 4 atoms; m represents an integer of 1 to 5; n represents an integer of 0 to 3; p represents an integer of 0 to 2; and *1 represents an asymmetric center.

  一种制备具有CCR5拮抗作用的光学活性亚砜衍生物（I）的方法，不会引起外消旋化和普默尔重排等副反应，包括将化合物（II）与化合物（III）反应，如下图所示：其中，R1代表氢、脂肪烃基或芳香基；R2代表卤素、烷基、羟基、氨基、芳香基等；R3代表5-或6-成员环；R4代表氢、烷基、烷氧基或卤素；R5代表氢、烃基、杂环基、酰基等；环A代表可选取代的苯环；X代表成分为1到4个原子的线性部分的键或二价基团；m代表1到5的整数；n代表0到3的整数；p代表0到2的整数；*1代表不对称中心。
• Process for producing optically active sulfoxide derivative
  申请人：Tawada Hiroyuki

  公开号：US20050107606A1

  公开（公告）日：2005-05-19

  A process for preparing an optically active sulfoxide derivative (I) having CCR5 antagonism without causing side reactions such as racemization and Pummerer rearrangement, which comprises reacting a compound (II) with a compound (III) as shown by the following scheme: wherein R 1 represents hydrogen, an aliphatic hydrocarbon group or an aromatic group; R 2 represents halogeno, alkyl, hydroxyl, amino, an aromatic group, etc.; R 3 represents a 5- or 6-membered ring; R 4 represents hydrogen, alkyl, alkoxy or halogeno; R 5 represents hydrogen, a hydrocarbon group, a heterocyclic group, acyl, etc.; ring A represents an optionally substituted benzene ring; X represents a bond or divalent group comprising a linear part constituted of 1 to 4 atoms; m represents an integer of 1 to 5; n represents an integer of 0 to 3; p represents an integer of 0 to 2; and * 1 represents an asymmetric center.

  一种制备具有CCR5拮抗作用的光学活性亚砜衍生物（I）的方法，不会引起外消旋和普默尔重排等副反应，包括将化合物（II）与化合物（III）按以下方案反应：其中R1代表氢、脂肪烃基或芳香族基；R2代表卤素、烷基、羟基、氨基、芳香族基等；R3代表5-或6-成员环；R4代表氢、烷基、烷氧基或卤素；R5代表氢、烃基、杂环基、酰基等；环A代表可选取代的苯环；X代表由1到4个原子构成的线性部分的键或双价基团；m代表1到5的整数；n代表0到3的整数；p代表0到2的整数；*1代表手性中心。
• Biphenyl compound as CCR2/CCR5 receptor antagonist
  申请人：Medshine Discovery Inc.

  公开号：US11155523B2

  公开（公告）日：2021-10-26

  Provided is a CCR2/CCR5 receptor antagonist and the use thereof in the preparation of a drug for treating diseases associated with the CCR2/CCR5. In particular, disclosed are a compound represented by formula (I) and a pharmaceutically acceptable salt thereof.

  本发明提供了一种 CCR2/CCR5 受体拮抗剂及其在制备治疗与 CCR2/CCR5 相关疾病的药物中的用途。特别是公开了由式（I）代表的化合物及其药学上可接受的盐。
• Unusual asymmetric oxidation of sulfide; the diastereoselective oxidation of prochiral sulfide-chiral acid salt with hydrogen peroxide without metal
  作者：Tomomi Ikemoto、Atsuko Nishiguchi、Tatsuya Ito、Hiroyuki Tawada

  DOI：10.1016/j.tet.2005.03.036

  日期：2005.5

  The sulfide 4 was treated with chiral acid in a mixture of toluene and methyl iso-butylketone to precipitate the salt, which reacted with 30% H2O2 for 3 weeks at rt. The resulting crystals were collected followed by recrystallization to give the salt of enantiometrically pure sulfoxide and chiral acid 7 in 72% yield and 98.1% de, which was led to chiral sulfoxide S-3 after neutralization. Sulfoxide S-3 was led to S-1a as the candidate for an orally active HIV-1 therapeutic agent. (c) 2005 Elsevier Ltd. All rights reserved.
• BICYCLIC COMPOUND, PRODUCTION AND USE THEREOF
  申请人：TOBIRA THERAPEUTICS, INC.

  公开号：US20190038604A1

  公开（公告）日：2019-02-07

  The present invention provides a new cyclic compound having a CCR antagonist activity, especially a CCR5 antagonist activity, and the use thereof. The compound of the present invention is represented by the formula: wherein, R 1 is a 5- to 6-membered ring group which may be substituted; X 1 is a bond or the like; ring A is a 5- to 6-membered ring group which may be substituted; ring B is a 8- to 10-membered ring group which may be substituted; X 2 is a bivalent group of 1 to 4 atoms; Z 1 is a bivalent cyclic ring group or the like; Z 2 is a bond or the like; and R 2 is an amino group, a nitrogen-containing heterocyclic group which may be substituted or the like, or a salt thereof.