(S)-2-(4-chlorobenzenesulfonylamino)-3-phenylpropanoic acid

• 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: (S)-2-(4-chlorobenzenesulfonylamino)-3-phenylpropanoic acid
• 英文别名: ((4-chlorophenyl)sulfonyl)phenylalanine；Nα-(4-chlorobenzenesulfonyl)-L-phenylalanine；N-[(4-chlorophenyl)sulfonyl]phenylalanine；(2S)-2-[(4-chlorophenyl)sulfonylamino]-3-phenylpropanoic acid
• 化学式: C₁₅H₁₄ClNO₄S
• mdl: MFCD00173003
• 分子量: 339.799
• InChiKey: JEDDEMYHWQZSLN-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-chlorobenzenesulfonylamino)-3-phenylpropanoic acid 以 乙二醇 为溶剂， 以32%的产率得到3,6-dibenzyl-1,4-bis((4-chlorophenyl)sulfonyl)piperazine-2,5-dione
  参考文献：
  名称：

  Development of Piperazinediones as dual inhibitor for treatment of Alzheimer's disease

  摘要：

  Novel multifunctional 3,6-Diphenyl-1,4-bis(phenylsulfonyl)piperazine-2,5-dione derivatives were designed and synthesized for the treatment of Alzheimer's disease (AD). The designed scaffold has blood brain barrier penetrating ability, acetylcholinesterase (AChE) and matrix metalloproteinase-2 (MMP-2) inhibition potential. Compounds 52 and 46 showed very significant inhibition against AChE, IC50 = 32.45 +/- 0.044, 28.65 +/- 0.029, BuChE, IC50 = 157.95 +/- 0.264, 160.58 +/- 0.082 and MMP-2, IC50 = 36.83 +/- 0.015, 19.57 +/- 0.005 (nM). In the enzyme kinetics study, lead molecule 46 showed noncompetitive inhibition of AChE with K-i = 7 nM and competitive inhibition of MMP-2 with K-i = 20 nM. Compounds 52 and 46 inhibited AChE-induced A beta aggregation at 20 mu M. The compounds also exhibited in-vitro antioxidant potential in DPPH assay. Further, compound 46 was found to be a promising neuroprotective agent in MC65 cells. Lead molecule 46 significantly enhanced working memory in scopolamine induced amnesia animal model at dose of 5 mg/kg dose. The mitochondrial membrane potential was restored in animals when treated with compounds 52 and 46. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.078
• 作为产物：
  描述：

  L-苯丙氨酸 、 4-氯苯磺酰氯 生成 (S)-2-(4-chlorobenzenesulfonylamino)-3-phenylpropanoic acid
  参考文献：
  名称：

  HIV protease inhibitors based on amino acid derivatives

  摘要：

  从以下组中选择的化合物，其中化合物I的化合物，化合物II的化合物，以及当化合物I和II的化合物包括其氨基团的药用可接受铵盐，其中R1、R2、Cx、n、R3、R4、R5、Y的定义如规范中所述。

  公开号：

  US20020151546A1

文献信息

• HIV protease inhibitors based on amino acid derivatives
  申请人：——

  公开号：US20020151546A1

  公开（公告）日：2002-10-17

  A compound selected from the group consisting of a compound of formula I 1 a compound of formula II 2 and when the compound of formula I and II comprises an amino group pharmaceutically acceptable ammonium salts thereof, wherein R 1 , R 2 , Cx, n, R 3 , R 4 , R 5 , Y are as defined in the specification.

  从以下组中选择的化合物，其中化合物I的化合物，化合物II的化合物，以及当化合物I和II的化合物包括其氨基团的药用可接受铵盐，其中R1、R2、Cx、n、R3、R4、R5、Y的定义如规范中所述。
• SULFONAMIDE COMPOUNDS USEFUL AS ADG RECEPTOR MODULATORS
  申请人：Grewal Gurmit

  公开号：US20090111860A1

  公开（公告）日：2009-04-30

  The present invention relates to compounds of formula (I) that mediate Edg, including Edg-1, processes for their preparation, pharmaceutical compositions containing them as the active ingredient, to their use as medicaments and to their use in the manufacture of medicaments for use in the treatment in warm-blooded animals such as humans of diseases that have a significant vascularization or inflammatory component such as in tumor-related diseases. The present invention also relates to compounds that inhibit a5bl, and also that exhibit appropriate selectivity profile(s) against other integrins.

  本发明涉及公式（I）的化合物，其介导Edg，包括Edg-1，其制备方法，包含它们作为活性成分的制药组合物，它们作为药物的用途以及它们用于制造用于治疗具有显著血管化或炎症成分的疾病的药物，如肿瘤相关疾病。本发明还涉及抑制a5bl的化合物，以及对其他整合素具有适当选择性谱的化合物。
• CHEMICAL COMPOUNDS
  申请人：Cowen Scott

  公开号：US20100197749A1

  公开（公告）日：2010-08-05

  The invention relates to chemical compounds of formula (I) and (II): or pharmaceutically acceptable salts thereof, which possess Edg-1 antagonistic activity and are accordingly useful for their anti-cancer activity and thus in methods of treatment of the human or animal body. The invention also relates to processes for the manufacture of said chemical compounds, to pharmaceutical compositions containing them and to their use in the manufacture of medicaments of use in the production of an anti-cancer effect in a warm-blooded animal such as man.

  本发明涉及公式(I)和(II)的化合物，或其药学上可接受的盐，具有Edg-1拮抗活性，因此在抗癌活性方面有用，并且在人体或动物体的治疗方法中使用。本发明还涉及制造上述化合物的过程，包含它们的制药组合物以及它们在制造用于在诸如人类之类的恒温动物中产生抗癌效应的药物中的用途。
• Process for preparing optically active piperazine derivatives and intermediates for preparation
  申请人：YAMAKAWA CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0710652A2

  公开（公告）日：1996-05-08

  Process for preparing optically active 2-piperazinecarboxylic acid derivatives, particularly S-enantiomer thereof, in high yield and high optical purity on industrial scale. As the optical resolving agents, easily accessible sulfonamides derived from selected optically active amino acids, such as N-tosyl-L-phenylalanine, N-tosyl-D-phenylglycine, N-tosyl-L-alanine or N-tosyl-L-valine, give excellent results. These resolving agents are stable and easily recovered from the reaction mixture and reused. Resolved 2-piperazinecarboxylic acid derivatives are preferably isolated as 4-t-butoxycarbonyl (Boc) derivatives. Diastereomeric salts (an example being shown below) formed as the intermediates of resolution are novel. [In the formula "Ar" stands for a phenyl or naphthyl group which may be substituted with one to three C1-C6 alkyl groups, halogen atoms, nitro or alkoxy groups; and n=0 or 1.]

  在工业规模上以高产率和高光学纯度制备光学活性 2-哌嗪羧酸衍生物，特别是其 S-对映体的工艺。作为光学分解剂，从选定的光学活性氨基酸（如 N-对甲苯磺酰基-L-苯丙氨酸、N-对甲苯磺酰基-D-苯甘氨酸、N-对甲苯磺酰基-L-丙氨酸或 N-对甲苯磺酰基-L-缬氨酸）中提取的易于获得的磺酰胺类物质效果极佳。这些分解剂非常稳定，很容易从反应混合物中回收并重复使用。溶解后的 2-哌嗪甲酸衍生物最好以 4-叔丁氧羰基（Boc）衍生物的形式分离出来。作为分解中间体形成的非对映异构盐（如下所示的一个例子）是新颖的。 [式中 "Ar "代表苯基或萘基，可被一至三个 C1-C6 烷基、卤素原子、硝基或烷氧基取代；n=0 或 1。］
• Hiv protease inhibitors based on amino acid derivatives
  申请人：Ambrilia Biopharma Inc.

  公开号：EP1803706A1

  公开（公告）日：2007-07-04

  The present application refers to a compound selected from the group consisting of a compound of formula I wherein the compounds No. 1 to 10, respectively, are defined as follows The compounds are useful in the treatment of HIV and HTLV infections.

  本申请涉及的化合物选自由式 I 所组成的组 其中 1 号至 10 号化合物分别定义如下 这些化合物可用于治疗 HIV 和 HTLV 感染。