2-amino-3-(3-chlorophenyl)propionic acid ethyl ester hydrochloride | 457654-55-6

• 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: 2-amino-3-(3-chlorophenyl)propionic acid ethyl ester hydrochloride
• 英文别名: Ethyl 2-amino-3-(3-chlorophenyl)propanoate Hydrochloride；ethyl 2-amino-3-(3-chlorophenyl)propanoate;hydrochloride
• CAS: 457654-55-6
• 化学式: C₁₁H₁₄ClNO₂*ClH
• mdl: MFCD28145319
• 分子量: 264.152
• InChiKey: HNZGZHRWNCDKDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 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：

  2-amino-3-(3-chlorophenyl)propionic acid ethyl ester hydrochloride 在 五氯化磷 、 三乙胺 、 乙酰氯 作用下， 以 乙酸乙酯 为溶剂， 反应 7.0h， 生成 3-(3-chlorophenyl)-2-{2-[(1H-indole-2-carbonyl)amino]benzoylamino}propionic acid ethyl ester
  参考文献：
  名称：

  Anthranilic acid based CCK1 receptor antagonists: preliminary investigation on their second “touch point”

  摘要：

  In this phase of structure-affinity relationship study of VL-0395, a new anthranilic acid based CCK1 selective antagonist, we propose a series Of Unnatural aminoacidic derivatives. The result of this work is the identification of a new CCK ligand, which possesses an affinity (IC50 = 35 nm) one order of magnitude greater than the lead and, as a general rule, it points out how the hypothesized receptorial pocket which accommodates the Phe residue allows much more structural modification than that interacting with the N-terminal group. Hence, the modification of the C-terminal pharmacophoric group of our lead VL-0395 can not only enhance the affinity of anthranific acid derivatives but can modulate the selectivity for one CCK receptor subtype or afford mixed antagonists. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.01.002
• 作为产物：
  描述：

  diethyl α-acetamido, α-(3-chlorobenzyl)malonate 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 2-amino-3-(3-chlorophenyl)propionic acid ethyl ester hydrochloride
  参考文献：
  名称：

  Anthranilic acid based CCK1 receptor antagonists: preliminary investigation on their second “touch point”

  摘要：

  In this phase of structure-affinity relationship study of VL-0395, a new anthranilic acid based CCK1 selective antagonist, we propose a series Of Unnatural aminoacidic derivatives. The result of this work is the identification of a new CCK ligand, which possesses an affinity (IC50 = 35 nm) one order of magnitude greater than the lead and, as a general rule, it points out how the hypothesized receptorial pocket which accommodates the Phe residue allows much more structural modification than that interacting with the N-terminal group. Hence, the modification of the C-terminal pharmacophoric group of our lead VL-0395 can not only enhance the affinity of anthranific acid derivatives but can modulate the selectivity for one CCK receptor subtype or afford mixed antagonists. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.01.002

文献信息

• An Old Story in the Parallel Synthesis World: An Approach to Hydantoin Libraries
  作者：Andrey V. Bogolubsky、Yurii S. Moroz、Olena Savych、Sergey Pipko、Angelika Konovets、Maxim O. Platonov、Oleksandr V. Vasylchenko、Vasyl V. Hurmach、Oleksandr O. Grygorenko

  DOI：10.1021/acscombsci.7b00163

  日期：2018.1.8

  An approach to the parallel synthesis of hydantoin libraries by reaction of in situ generated 2,2,2-trifluoroethylcarbamates and α-amino esters was developed. To demonstrate utility of the method, a library of 1158 hydantoins designed according to the lead-likeness criteria (MW 200–350, cLogP 1–3) was prepared. The success rate of the method was analyzed as a function of physicochemical parameters

  开发了一种通过原位生成的2,2,2-三氟乙基氨基甲酸酯与α-氨基酯反应平行合成乙内酰脲文库的方法。为了证明该方法的实用性，准备了根据铅样标准（MW 200–350，cLogP 1-3）设计的1158个乙内酰脲文库。分析了该方法的成功率与产品理化参数的关系，发现该方法可以被认为是用于铅导向合成的工具。通过合理设计，使用开发的方法进行平行合成，计算机模拟和体外筛选相结合的方法，发现了一种含乙内酰脲的超微摩尔主要分子，可作为Aurora激酶A抑制剂。
• Asymmetric catalytic alkynylation of thiazolones and azlactones for synthesis of quaternary α-amino acid precursors
  作者：Beibei Meng、Qian Shi、Yuan Meng、Jie Chen、Weiguo Cao、Xiaoyu Wu

  DOI：10.1039/d1ob00582k

  日期：——

  Asymmetric alkynylation of thiazolones and azlactones with alkynylbenziodoxolones as the electrophilic alkyne source catalyzed by thiourea phosphonium salt is described. By using thiazolones as nucleophiles, the desired alkyne functionalized thiazolones were obtained in 55–89% yields with 31–86% ee. Azlactones gave the desired products in comparable yields with lower enantioselectivities. Ring-opening

  描述了硫脲鏻盐催化的噻唑酮和吖内酯的不对称炔基化反应，其中炔基苯并氧唑酮作为亲电炔烃源。通过使用噻唑酮作为亲核试剂，以 55-89% 的产率和 31-86% 的 ee 获得所需的炔烃官能化噻唑酮。Azlactones 以较低的对映选择性以相当的产率得到所需的产物。炔基化产物的开环导致α，α-二取代的α-氨基酸衍生物有效而不会损失对映选择性。
• Anthranilic acid based CCK1 receptor antagonists: preliminary investigation on their second “touch point”
  作者：Antonio Varnavas、Lucia Lassiani、Valentina Valenta、Laura Mennuni、Francesco Makovec、Dimitra Hadjipavlou-Litina

  DOI：10.1016/j.ejmech.2005.01.002

  日期：2005.6

  In this phase of structure-affinity relationship study of VL-0395, a new anthranilic acid based CCK1 selective antagonist, we propose a series Of Unnatural aminoacidic derivatives. The result of this work is the identification of a new CCK ligand, which possesses an affinity (IC50 = 35 nm) one order of magnitude greater than the lead and, as a general rule, it points out how the hypothesized receptorial pocket which accommodates the Phe residue allows much more structural modification than that interacting with the N-terminal group. Hence, the modification of the C-terminal pharmacophoric group of our lead VL-0395 can not only enhance the affinity of anthranific acid derivatives but can modulate the selectivity for one CCK receptor subtype or afford mixed antagonists. (c) 2005 Elsevier SAS. All rights reserved.