(S)-1-(5-苯基-1H-咪唑-2-基)乙胺 | 864825-23-0

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (S)-1-(5-苯基-1H-咪唑-2-基)乙胺
• 中文别名: 伊卢多啉中间体4；(alphaS)-alpha-甲基-4-苯基-1H-咪唑-2-甲胺
• 英文名称: (S)-1-(4-phenyl-1H-imidazol-2-yl)ethanamine
• 英文别名: 1-(4-phenyl-1H-imidazole-2-yl)ethyl amine；(1S)-1-(5-phenyl-1H-imidazol-2-yl)ethanamine
• CAS: 864825-23-0
• 化学式: C₁₁H₁₃N₃
• 分子量: 187.244
• InChiKey: XQFMQMXJXWTGON-QMMMGPOBSA-N

物化性质

• 熔点：
  136-138°C
• 沸点：
  422.1±28.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H319
• 储存条件：
  存储条件：2-8℃，避光保存，并在惰性气体环境中存放。

制备方法与用途

(S)-1-(5-苯基-1H-咪唑-2-基)乙胺是一种胺类有机物，可作为医药中间体使用。

反应信息

• 作为反应物：
  描述：

  (S)-1-(5-苯基-1H-咪唑-2-基)乙胺 在 盐酸 、 sodium tetrahydroborate 、 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 、 甲醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Identification of a dual δ OR antagonist/μ OR agonist as a potential therapeutic for diarrhea-predominant Irritable Bowel Syndrome (IBS-d)

  摘要：

  A small set of acyclic analogs 5 were prepared to explore their structure-activity relationships (SARs) relative to heterocyclic core, opioid receptor (OR) agonists 4. Compound 5l was found to have very favorable OR binding affinities at the δ and μ ORs (r K(i) δ=1.3 nM; r K(i) μ=0.9 nM; h K(i) μ=1.7 nM), with less affinity for the κ OR (gp K(i) κ=55 nM). The OR functional profile for 5l varied from the previously described dual δ/μ OR agonists 4, with 5l being a potent, mixed dual δ OR antagonist/μ OR agonist [δ IC(50)=89 nM (HVD); μ EC(50)=1 nM (GPI); κ EC(50)=1.6 μM (GPC)]. Compound 5l has progressed through a clinical Phase II Proof of Concept study on 800 patients suffering from diarrhea-predominant Irritable Bowel Syndrome (IBS-d). This Phase II study was recently completed successfully, with 5l demonstrating statistically significant efficacy over placebo.

  DOI：

  10.1016/j.bmcl.2012.05.042
• 作为产物：
  描述：

  2-氨基苯乙酮盐酸盐 在 N-甲基吗啉 、 palladium 10% on activated carbon 、 ammonium acetate 、 氢气 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (S)-1-(5-苯基-1H-咪唑-2-基)乙胺
  参考文献：
  名称：

  Identification of a dual δ OR antagonist/μ OR agonist as a potential therapeutic for diarrhea-predominant Irritable Bowel Syndrome (IBS-d)

  摘要：

  A small set of acyclic analogs 5 were prepared to explore their structure-activity relationships (SARs) relative to heterocyclic core, opioid receptor (OR) agonists 4. Compound 5l was found to have very favorable OR binding affinities at the δ and μ ORs (r K(i) δ=1.3 nM; r K(i) μ=0.9 nM; h K(i) μ=1.7 nM), with less affinity for the κ OR (gp K(i) κ=55 nM). The OR functional profile for 5l varied from the previously described dual δ/μ OR agonists 4, with 5l being a potent, mixed dual δ OR antagonist/μ OR agonist [δ IC(50)=89 nM (HVD); μ EC(50)=1 nM (GPI); κ EC(50)=1.6 μM (GPC)]. Compound 5l has progressed through a clinical Phase II Proof of Concept study on 800 patients suffering from diarrhea-predominant Irritable Bowel Syndrome (IBS-d). This Phase II study was recently completed successfully, with 5l demonstrating statistically significant efficacy over placebo.

  DOI：

  10.1016/j.bmcl.2012.05.042

文献信息

• Novel compounds as opioid receptor modulators
  申请人：Breslin J. Henry

  公开号：US20050203143A1

  公开（公告）日：2005-09-15

  The present invention is directed to novel opioid receptor modulators of Formula (I). The invention further relates to methods for preparing such compounds, pharmaceutical compositions containing them, and their use in the treatment of disorders that may be ameliorated or treated by the modulation of opioid receptors.

  本发明涉及式(I)的新型阿片受体调节剂。该发明进一步涉及制备这类化合物的方法、包含它们的药物组合物，以及它们在治疗可通过调节阿片受体得到改善或治疗的疾病中的用途。
• Process for the preparation of opioid modulators
  申请人：Cai Chaozhong

  公开号：US20060211861A1

  公开（公告）日：2006-09-21

  The present invention is directed to novel processes for the preparation of opioid modulators (agonists and antagonists) and intermediates in their synthesis. The opioid modulators are useful for the treatment and prevention of as pain and gastrointestinal disorders.

  本发明涉及用于制备阿片类药物调节剂（激动剂和拮抗剂）及其合成中间体的新工艺。这些阿片类药物调节剂可用于治疗和预防疼痛和胃肠道疾病。
• [EN] PROCESS FOR THE PREPARATION OF INTERMEDIATES USEFUL IN THE SYNTHESIS OF ELUXADOLINE<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION D'INTERMÉDIAIRES UTILES POUR LA SYNTHÈSE D'ELUXADOLINE
  申请人：ACTAVIS GROUP PTC EHF

  公开号：WO2016135756A1

  公开（公告）日：2016-09-01

  The invention relates to an improved process for preparing [(S)-1-(4-phenyl-1-H-imidazol-2- yl)-ethyl]-amine. The process involves formation of the novel intermediate crystalline compound[(S)-1-(4-phenyl-1-H-imidazol-2-yl)-ethyl]-carbamic acid tert-butyl ester oxalate.

  本发明涉及一种改进的制备[(S)-1-(4-苯基-1H-咪唑-2-基)-乙基]-胺的方法。该工艺涉及形成新型中间结晶化合物[(S)-1-(4-苯基-1H-咪唑-2-基)-乙基]-氨基甲酸叔丁酯草酸盐。
• [EN] NOVEL SUBSTITUTED AMIDES OF TRITERPENE DERIVATIVES AS HIV INHIBITORS<br/>[FR] NOUVEAUX AMIDES SUBSTITUÉS DE DÉRIVÉS DE TRITERPÈNE UTILISÉS COMME INHIBITEURS DU VIH
  申请人：HETERO RESEARCH FOUNDATION

  公开号：WO2017021922A1

  公开（公告）日：2017-02-09

  The present invention relates to compounds of novel substituted amides of triteripene derivatives of formula (I); or pharmaceutically acceptable salts, pharmaceutically acceptable solvates, pharmaceutically acceptable hydrates, tautomers, stereoisomers, prodrugs, compositions or combination thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, X, Y, Z1, Z2, Z3 and formula (II) are as defined herein. The present invention also relates to,, and pharmaceutical compositions comprising compounds of formula (I) useful for the treatment of viral diseases and particularly HIV mediated diseases.

  本发明涉及一种新型取代酰胺衍生物化合物，其为式（I）的三萜衍生物；或药学上可接受的盐、药学上可接受的溶剂化合物、药学上可接受的水合物、互变异构体、立体异构体、前药、组合物或它们的组合，其中R1、R2、R3、R4、R5、R6、R7、R8、X、Y、Z1、Z2、Z3和式（II）如本文所定义。本发明还涉及，以及包含式（I）化合物的制药组合物，用于治疗病毒性疾病，特别是HIV介导的疾病。
• [EN] PEPTIDOMIMETIC PROTEASOME INHIBITORS<br/>[FR] INHIBITEURS PEPTIDOMIMÉTIQUES DU PROTÉASOME
  申请人：UNIV CORNELL

  公开号：WO2019075252A1

  公开（公告）日：2019-04-18

  The compounds of the present invention are represented by the following compounds having Formula (I) and Formula (I'): where the substituents R, R1, R3 R4, R', W, X, Y, Z, k, and m are as defined herein and where the substituents R, R1, R2, R3, R4, X, Y, Z, and m are as defined herein. These compounds are used in the treatment of bacterial infections, parasite infections, fungal infections, cancer, immunologic disorders, autoimmune disorders, neurodegenerative diseases and disorders, inflammatory disorders, or muscular dystrophy or for providing immunosuppression for transplanted organs or tissues.

  本发明的化合物由具有式（I）和式（I'）的以下化合物表示：其中取代基R、R1、R3、R4、R'、W、X、Y、Z、k和m如本文所定义，取代基R、R1、R2、R3、R4、X、Y、Z和m如本文所定义。这些化合物用于治疗细菌感染、寄生虫感染、真菌感染、癌症、免疫紊乱、自身免疫性疾病、神经退行性疾病和紊乱、炎症性疾病，或肌肉萎缩症，或用于为移植的器官或组织提供免疫抑制。