(βS)-β-氨基-2-氯苯丙醇 | 103616-91-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (βS)-β-氨基-2-氯苯丙醇
• 中文别名: 苯丙醇,b-氨基-2-氯-,(S)-；L-2-氯苯丙氨醇
• 英文名称: (S)-2-amino-3-(2-chlorophenyl)propan-1-ol
• 英文别名: 2-chloro-L-phenylalaninol；(2S)-2-Amino-3-(2-chlorophenyl)propan-1-OL
• CAS: 103616-91-7
• 化学式: C₉H₁₂ClNO
• 分子量: 185.653
• InChiKey: BTYIMXKEQJVRSF-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  L-2-氯苯丙氨酸	2-chloro-L-phenylalanine	103616-89-3	C9H10ClNO2	199.637

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(S)-4-(2-chlorobenzyl)-4,5-dihydrooxazol-2-ylamine	1043922-41-3	C10H11ClN2O	210.663
  ——	(S)-tert-butyl 1-(2-chlorophenyl)-3-hydroxypropan-2-ylcarbamate	944470-58-0	C14H20ClNO3	285.771

反应信息

• 作为反应物：
  描述：

  (βS)-β-氨基-2-氯苯丙醇 、 二碳酸二叔丁酯 以 氯仿 为溶剂， 以98%的产率得到(S)-tert-butyl 1-(2-chlorophenyl)-3-hydroxypropan-2-ylcarbamate
  参考文献：
  名称：

  New thiazole carboxamides as potent inhibitors of Akt kinases

  摘要：

  A new series of 2-substituted thiazole carboxamides were identified as potent pan inhibitors against all three isoforms of Akt (Akt1, Akt2 and Akt3) by systematic optimization of weak screening hit N-(1-amino-3-phenylpropan-2-yl)-2-phenylthiazole-5-carboxamide (1). One of the most potent compounds, 5m, inhibited the kinase activities of Akt1, Akt2 and Akt3 with IC50 values of 25, 196 and 24 nM, respectively. The compound also potently inhibited the phosphorylation of downstream MDM2 and GSK3 beta proteins, and displayed strongly antiproliferative activity in prostate cancer cells. The inhibitors might serve as lead compounds for further development of novel effective anticancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.080
• 作为产物：
  描述：

  L-2-氯苯丙氨酸 在 锂硼氢 、 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(βS)-β-氨基-2-氯苯丙醇
  参考文献：
  名称：

  New thiazole carboxamides as potent inhibitors of Akt kinases

  摘要：

  A new series of 2-substituted thiazole carboxamides were identified as potent pan inhibitors against all three isoforms of Akt (Akt1, Akt2 and Akt3) by systematic optimization of weak screening hit N-(1-amino-3-phenylpropan-2-yl)-2-phenylthiazole-5-carboxamide (1). One of the most potent compounds, 5m, inhibited the kinase activities of Akt1, Akt2 and Akt3 with IC50 values of 25, 196 and 24 nM, respectively. The compound also potently inhibited the phosphorylation of downstream MDM2 and GSK3 beta proteins, and displayed strongly antiproliferative activity in prostate cancer cells. The inhibitors might serve as lead compounds for further development of novel effective anticancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.080

文献信息

• Discovery and Characterization of 2-Aminooxazolines as Highly Potent, Selective, and Orally Active TAAR1 Agonists
  作者：Guido Galley、Angélica Beurier、Guillaume Décoret、Annick Goergler、Roman Hutter、Susanne Mohr、Axel Pähler、Philipp Schmid、Dietrich Türck、Robert Unger、Katrin Groebke Zbinden、Marius C. Hoener、Roger D. Norcross

  DOI：10.1021/acsmedchemlett.5b00449

  日期：2016.2.11

  ligands. Starting from a known adrenergic compound 1, structural modifications were made to obtain highly potent and selective TAAR1 ligands such as 12 (RO5166017), 18 (RO5256390), 36 (RO5203648), and 48 (RO5263397). These compounds exhibit drug-like physicochemical properties, have good oral bioavailability, and display in vivo activity in a variety of animal models relevant for psychiatric diseases

  发现2-氨基恶唑啉是TAAR1配体的新型结构类别。从已知的肾上腺素化合物1开始，进行了结构修饰，以获得高效且选择性的TAAR1配体，例如12（RO5166017），18（RO5256390），36（RO5203648）和48（RO5263397）。这些化合物表现出类似药物的理化性质，具有良好的口服生物利用度，并且在与精神疾病和成瘾有关的多种动物模型中显示出体内活性。
• Rational Design of Selective and Bioactive Inhibitors of the <i>Mycobacterium tuberculosis</i> Proteasome
  作者：Kyle A. Totaro、Dominik Barthelme、Peter T. Simpson、Xiuju Jiang、Gang Lin、Carl F. Nathan、Robert T. Sauer、Jason K. Sello

  DOI：10.1021/acsinfecdis.6b00172

  日期：2017.2.10

  The 20S core particle of the proteasome in Mycobacterium tuberculosis (Mtb) is a promising, yet unconventional, drug target. This multimeric peptidase is not essential, yet degrades proteins that have become damaged and toxic via reactions with nitric oxide (and/or the associated reactive nitrogen intermediates) produced during the host immune response. Proteasome inhibitors could render Mtb susceptible

  结核分枝杆菌（Mtb）中蛋白酶体的20S核心颗粒是有前途的但非常规的药物靶标。该多聚体肽酶不是必需的，而是通过与宿主免疫应答过程中产生的一氧化氮（和/或相关的反应性氮中间体）反应，降解已受损且有毒的蛋白质。蛋白酶体抑制剂可以使Mtb对免疫系统敏感，但只有在不抑制人类必需的20S对应物的情况下，它们才在治疗上可行。Mtb的选择性抑制剂设计和合成20S是基于其独特的底物偏好和模仿丁香脂素的真核蛋白酶体的模拟底物的共价抑制剂的结构。与亲本丁香脂素不同，设计的类似物弱抑制人类20S（Hs 20S）蛋白酶体，比人类对应物优先抑制Mtb 20S多达74倍。此外，它们可以穿透分枝杆菌的细胞包膜并使Mtb易受一氧化氮介导的压力的影响。重要的是，它们不会在体外抑制人细胞系的生长，因此可能是结核药物开发的起点。
• [EN] COMPOUNDS COMPRISING A FIBROBLAST ACTIVATION PROTEIN LIGAND AND USE THEREOF<br/>[FR] COMPOSÉS COMPRENANT UN LIGAND DE PROTÉINE D'ACTIVATION DES FIBROBLASTES ET LEUR UTILISATION
  申请人：3B PHARMACEUTICALS GMBH

  公开号：WO2022148843A1

  公开（公告）日：2022-07-14

  The present invention is related to a compound comprising a cyclic peptide of formula (I) and an N-terminal modification group A attached to Xaa1, wherein each and any one of Xaa1, Xaa2, Xaa3, Xaa4, Xaa5, Xaa6 and Xaa7 is a residue of an amino acid, and Yc is a structure of formula (X).

  本发明涉及一种化合物，该化合物包括公式（I）的环肽和附加在Xaa1上的N-末端修饰基团A，其中Xaa1、Xaa2、Xaa3、Xaa4、Xaa5、Xaa6和Xaa7中的任何一个都是氨基酸残基，而Yc是公式（X）的结构。
• Hydroxymorpholinone derivative and medicinal use thereof
  申请人：Nakamura Masayuki

  公开号：US20050176704A1

  公开（公告）日：2005-08-11

  A compound represented by the following formula (I) wherein R 1 and R 2 are each a lower alkyl group optionally having substituents, which has a calpain inhibitory activity, or a salt thereof is provided.

  下式(I)代表的化合物 其中 R 1 和 R 2 均为可选具有取代基的低级烷基，具有钙蛋白酶抑制活性的化合物或其盐。
• HYDROXYMORPHOLINONE DERIVATIVE AND MEDICINAL USE THEREOF
  申请人：Senju Pharmaceutical Co., Ltd.

  公开号：EP1491537B1

  公开（公告）日：2010-07-07