(R)-2-chlorophenylalanine methyl ester hydrochloride | 457654-72-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-chlorophenylalanine methyl ester hydrochloride
• 英文别名: 2-Chloro-d-phenylalanine methyl ester hcl；methyl (2R)-2-amino-3-(2-chlorophenyl)propanoate;hydrochloride
• CAS: 457654-72-7
• 化学式: C₁₀H₁₂ClNO₂*ClH
• 分子量: 250.125
• InChiKey: FXIXAZXWVBFVDS-SBSPUUFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-chlorophenylalanine methyl ester hydrochloride 在 [Rh(OH)(cod)]2 、 (S,R)-PPF-P(t-Bu)2 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 3-(2-chlorobenzyl)-4-((2-nitrophenyl)sulfonyl)-3,4,4a,10b-tetrahydro-2H-naphtho[1,2-b][1,4]oxazin-2-one
  参考文献：
  名称：

  铑通过氧杂双环烯烃的不对称开环-内酯化级联催化铑催化对映选择性合成恶嗪酮。

  摘要：

  铑催化的氧杂双环烯烃的不对称开环反应是合成手性杂环的有效方法。我们证明手性催化剂与手性氨基酸衍生的前亲核试剂的成对组合导致非对映体羟基酯的立体发散合成。有利的构象偏好诱导一种非对映异构体随后的内酯​​化，从而导致恶二酮的高度对映选择性合成。

  DOI：

  10.1021/acs.orglett.9b02819
• 作为产物：
  描述：

  methyl (2R)-3-(2-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 (R)-2-chlorophenylalanine methyl ester hydrochloride
  参考文献：
  名称：

  通过对苯丙氨酸衍生物的串联环化来形成吡嗪异喹啉骨架的非对映选择性：光学活性吡嗪异喹啉的简便合成

  摘要：

  基于对映体纯苯丙氨酸衍生物的串联环化，研究了一种光学活性吡嗪异喹啉骨架的简便且立体控制的结构。该反应以优异的非对映选择性提供了光学活性的6,11b-反式吡嗪并异喹啉环系统，该方法适用于具有多种取代基的苯丙氨酸衍生物的环化。

  DOI：

  10.1016/j.tet.2014.04.045

文献信息

• HETEROCYCLIC COMPOUNDS USEFUL IN THE TREATMENT OF DISEASE
  申请人：EPIGEN BIOSCIENCES, INC.

  公开号：US20160024031A1

  公开（公告）日：2016-01-28

  Heterocyclic compounds are described that are lysophosphatidic acid receptor ligands that are useful in the treatment of lysophosphatidic acid receptor-dependent diseases and conditions, including but not limited to diseases involving fibrosis, such as fibrosis of the heart, kidney, liver and lung, and scleroderma; inflammatory diseases such as diabetic nephropathy and inflammatory bowel disease; ocular diseases such as diseases involving retinal degeneration; nerve diseases such as pruritus and pain. Non-limiting examples of those compounds include (RS)-3-Cyclopropyl-2-4-[3-methyl-4((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-benzyloxy}-propionic acid and (R)-1-(4′-5-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-4-fluoro-pyrazol-1-yl}-2-fluoro-biphenyl-4-yl)-cyclopropanecarboxylic acid.

  描述了异环化合物，这些化合物是溶血磷脂酸受体配体，可用于治疗溶血磷脂酸受体依赖性疾病和状况，包括但不限于涉及纤维化的疾病，如心脏、肾脏、肝脏和肺的纤维化以及硬化病；炎症性疾病，如糖尿病肾病和炎症性肠病；眼病，如涉及视网膜变性的疾病；神经疾病，如瘙痒和疼痛。这些化合物的非限制性例子包括(RS)-3-环丙基-2-4-[3-甲基-4((R)-1-苯基-乙氧羰基氨基)-异恶唑-5-基]-苄氧基}-丙酸和(R)-1-(4′-5-[1-(2-氯-苯基)-乙氧羰基氨基]-4-氟-吡唑-1-基}-2-氟-联苯-4-基)-环丙烷甲酸。
• Identification and initial optimization of inhibitors of Clostridium difficile (C. difficile) toxin B (TcdB)
  作者：Jeffrey J. Letourneau、Ilana L. Stroke、David W. Hilbert、Laurie J. Sturzenbecker、Brett A. Marinelli、Jorge G. Quintero、Joan Sabalski、Linh Ma、David J. Diller、Philip D. Stein、Maria L. Webb

  DOI：10.1016/j.bmcl.2018.01.005

  日期：2018.2

  The discovery, synthesis and preliminary structure-activity relationship (SAR) of a novel class of inhibitors of Clostridium difficile (C. difficile) toxin B (TcdB) is described. A high throughput screening (HTS) campaign resulted in the identification of moderately active screening hits 1–5 the most potent of which was compound 1 (IC50 = 0.77 µM). In silico docking of an early analog offered suggestions

  一类新的抑制剂的发现，合成和初步结构-活性关系（SAR）艰难梭菌（艰难梭菌）毒素B（TcdB的）进行说明。一种高通量筛选（HTS）运动导致中等活性筛选命中的标识1 - 5，其最有效的是化合物1（IC 50  = 0.77微米）。在计算机对接中，早期的类似物为结构修饰提供了建议，从而导致设计和合成了高效的类似物13j（IC 50  = 1 nM）和13 l（IC 50 = 7 nM）作为进一步优化的线索。
• Heterocyclic compounds useful in the treatment of disease
  申请人：EPIGEN BIOSCIENCES, INC.

  公开号：US10000459B2

  公开（公告）日：2018-06-19

  Heterocyclic compounds are described that are lysophosphatidic acid receptor ligands that are useful in the treatment of lysophosphatidic acid receptor-dependent diseases and conditions, including but not limited to diseases involving fibrosis, such as fibrosis of the heart, kidney, liver and lung, and scleroderma; inflammatory diseases such as diabetic nephropathy and inflammatory bowel disease; ocular diseases such as diseases involving retinal degeneration; nerve diseases such as pruritus and pain. Non-limiting examples of those compounds include (RS)-3-Cyclopropyl-2-4-[3-methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-benzyloxy}-propionic acid and (R)-1-(4′-5-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-4-fluoro-pyrazol-1-yl}-2-fluoro-biphenyl-4-yl)-cyclopropanecarboxylic acid.

  所述杂环化合物是溶血磷脂酸受体配体，可用于治疗溶血磷脂酸受体依赖性疾病和病症，包括但不限于涉及纤维化的疾病，如心脏、肾脏、肝脏和肺部纤维化以及硬皮病；炎症性疾病，如糖尿病肾病和炎症性肠病；眼部疾病，如涉及视网膜变性的疾病；神经疾病，如瘙痒和疼痛。这些化合物的非限制性实例包括 (RS)-3-Cyclopropyl-2-4-[3-methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-benzyloxy}- 丙酸和 (R)-3-Cyclopropyl-2-4-[3-methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-benzyloxy}- 丙酸。丙酸和(R)-1-(4′-5-[1-(2-氯苯基)-乙氧羰基氨基]-4-氟吡唑-1-基}-2-氟联苯-4-基)-环丙烷羧酸。
• Heterocyclic Compounds Useful In The Treatment of Disease
  申请人：EPIGEN BIOSCIENCES, INC.

  公开号：US20180297962A1

  公开（公告）日：2018-10-18

  Heterocyclic compounds are described that are lysophosphatidic acid receptor ligands that are useful in the treatment of lysophosphatidic acid receptor-dependent diseases and conditions, including but not limited to diseases involving fibrosis, such as fibrosis of the heart, kidney, liver and lung, and scleroderma; inflammatory diseases such as diabetic nephropathy and nonalcoholic steatohepatitis (NASH); ocular diseases such as diseases involving retinal degeneration; nerve diseases such as pruritus and pain.
• Heterocyclic Compounds Useful In The Treatment Of Disease
  申请人：EPIGEN BIOSCIENCES, INC.

  公开号：US20190135767A1

  公开（公告）日：2019-05-09

  A method for treating a lysophosphatidic acid-dependent disease or condition in a subject in need thereof is provided. The method includes administering to the subject a therapeutically effective amount of a heterocyclic compound. The heterocyclic compound is a lysophosphatidic acid receptor ligand. Lysophosphatidic acid-dependent diseases and conditions include diseases involving fibrosis, such as fibrosis of the heart, kidney, liver and lung, and scleroderma; inflammatory diseases such as diabetic nephropathy and inflammatory bowel disease; ocular diseases such as diseases involving retinal degeneration; nerve diseases such as pruritus and pain.