(3-cyano)-L-phenylalanine methyl ester hydrochloride

• 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: (3-cyano)-L-phenylalanine methyl ester hydrochloride
• 英文别名: H-Phe(3-CN)-OMe*HCl；(S)-2-amino-3-(3-cyano-phenyl)-propionic acid methyl ester hydrochloride；(s)-3-(3-cyanophenyl)alanine methyl ester hydrochloride；(D,L)-3-cyanophenylalanine methyl ester hydrochloride；H-Phe(3-CN)-OMe hydrochloride；3-cyano-L-phenylalanine methyl ester hydrochloride；methyl (2S)-2-amino-3-(3-cyanophenyl)propanoate;hydrochloride
• 化学式: C₁₁H₁₂N₂O₂*ClH
• 分子量: 240.689
• InChiKey: XXZHQCDQCKLSAF-PPHPATTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-cyano)-L-phenylalanine methyl ester hydrochloride 在 N-甲基吗啉 、 盐酸 、 氯化亚砜 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 N-[(2S)-1-(4-acetylpiperazin-1-yl)-3-(3-cyanophenyl)-1-oxopropan-2-yl]naphthalene-2-sulfonamide
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Potent Thrombin Inhibitors:  Piperazides of 3-Amidinophenylalanine

  摘要：

  Thrombin is the key enzyme in the blood coagulation system, and inhibitors of its proteolytic activity are of therapeutic interest since they are potential anticoagulants. The most potent inhibitor of the benzamidine type is N-alpha-[(2-naphthylsulfonyl)glycyl]-4-amidinophenylalanylpiperidide (NAPAP). However, NAPAP and other benzamidine derivatives do not show favorable pharmacological properties; above all, they have very low systemic bioavailability after oral administration. The goal of designing new compounds was to obtain potent inhibitors with improved pharmacokinetic properties. Piperazide derivatives of 3-amidinophenylalanine as the key building block were synthesized. The piperazine moiety opened the possibility to introduce quite different substituents on the second nitrogen using common synthetic procedures. Some of the newly synthesized compounds are potent inhibitors of thrombin and offer an approach to study structure-function relationships for inhibition of thrombin and related enzymes and for the improvement of their pharmacokinetic properties.

  DOI：

  10.1021/jm960668h
• 作为产物：
  描述：

  甲醇 、 L-3-氰基苯丙氨酸 在 氯化亚砜 作用下， 反应 3.67h， 以89%的产率得到(3-cyano)-L-phenylalanine methyl ester hydrochloride
  参考文献：
  名称：

  精氨酸模仿β-氨基酸β 3 hPhe（3-H 2 N-CH 2）如S1的配体在基于cyclotheonamide-β-类胰蛋白酶抑制剂

  摘要：

  近年来，β-胰蛋白酶是一种具有胰蛋白酶样活性的肥大细胞特异性丝氨酸蛋白酶，已成为变应性炎症领域中一种有希望的新型治疗靶标。最近，我们通过实施碱性P3残基开发了一种基于天然产物环乙酰胺E4的有效且选择性的β-胰蛋白酶抑制剂，该残基解决了β-胰蛋白酶扩展底物特异性的决定因素。为了进一步改善该前导结构的亲和力/选择性，我们现在研究了β-高-3-氨基甲基苯基丙氨酸作为S1配体。与衍生自赖氨酸或精氨酸的相应β-高氨基酸相反，我们证明该特定的碱性β-高氨基酸是开发β-胰蛋白酶抑制剂的优先S1配体。除了亲和力，选择性和降低的碱性外，

  DOI：

  10.1016/j.bmc.2011.09.050

文献信息

• Sulfonamide compounds
  申请人：Allison Brett

  公开号：US20060069286A1

  公开（公告）日：2006-03-30

  Certain sulfonamide compounds are dual CCK1/CCK2 inhibitors useful in the treatment of CCK1/CCK2 mediated diseases.

  某些磺酰胺化合物是双CCK1/CCK2抑制剂，在治疗CCK1/CCK2介导的疾病中很有用。
• META-SUBSTITUTED PHENYL SULFONYL AMIDES OF SECONDARY AMINO ACID AMIDES, THE PRODUCTION THEREOF, AND USE THEREOF AS MATRIPTASE INHIBITORS
  申请人：Steinmetzer Torsten

  公开号：US20100305090A1

  公开（公告）日：2010-12-02

  The invention relates to meta-substituted phenyl sulfonyl amides of secondary amino acid amides according to the general formula (I), (II), or (III), the production thereof, and the use thereof as matriptase inhibitors, in particular the use thereof as drugs for inhibiting tumor growth and/or metastasization.

  该发明涉及通式（I）、（II）或（III）的次级氨基酸酰胺的亚苯基磺酰胺，其制备方法以及其作为matriptase抑制剂的用途，特别是其作为抑制肿瘤生长和/或转移的药物的用途。
• Factor xa inhibitors with aryl-amidines and derivatives, and prodrugs thereof
  申请人：——

  公开号：US20030065176A1

  公开（公告）日：2003-04-03

  The present invention relates to a compound with aryl-amidines, particularly amidinoaryl-cyclopropanes, amidinoarylmethyl-pyrroles, amidinoaryl-benzenes, amidinoaryl-pyridines, or amindonoaryl-alanines, represented by formula (1), a pharmaceutically acceptable salt, a prodrug, a hydrate, a solvate or an isomer thereof, which are inhibitors of coagulation enzyme, factor Xa (FXa). The present invention also relates to a pharmaceutical composition containing the compound, and a method of using the same as an anticoagulant agent for treatment and prevention of thrombosis disorders.

  本发明涉及一种具有芳基胺基的化合物，特别是表示为式（1）的芳基胺基环丙烷，芳基胺基甲基吡咯烷，芳基胺基苯，芳基胺基吡啶或芳基胺基丙氨酸的化合物，其为凝血酶Xa（FXa）的抑制剂，包括药用盐、前药、水合物、溶剂合物或其异构体。本发明还涉及含有该化合物的药物组合物，以及将其用作抗凝血剂治疗和预防血栓症障碍的方法。
• The arginine mimicking β-amino acid β3hPhe(3-H2N-CH2) as S1 ligand in cyclotheonamide-based β-tryptase inhibitors
  作者：Dennis Janke、Christian P. Sommerhoff、Norbert Schaschke

  DOI：10.1016/j.bmc.2011.09.050

  日期：2011.12

  β-Tryptase, a mast-cell specific serine protease with trypsin-like activity, has emerged in the last years as a promising novel therapeutic target in the field of allergic inflammation. Recently, we have developed a potent and selective β-tryptase inhibitor based on the natural product cyclotheonamide E4 by implementing a basic P3 residue that addresses the determinants of the extended substrate specificity

  近年来，β-胰蛋白酶是一种具有胰蛋白酶样活性的肥大细胞特异性丝氨酸蛋白酶，已成为变应性炎症领域中一种有希望的新型治疗靶标。最近，我们通过实施碱性P3残基开发了一种基于天然产物环乙酰胺E4的有效且选择性的β-胰蛋白酶抑制剂，该残基解决了β-胰蛋白酶扩展底物特异性的决定因素。为了进一步改善该前导结构的亲和力/选择性，我们现在研究了β-高-3-氨基甲基苯基丙氨酸作为S1配体。与衍生自赖氨酸或精氨酸的相应β-高氨基酸相反，我们证明该特定的碱性β-高氨基酸是开发β-胰蛋白酶抑制剂的优先S1配体。除了亲和力，选择性和降低的碱性外，
• Novel urokinase inhibitors
  申请人：Wilex AG

  公开号：US20030013723A1

  公开（公告）日：2003-01-16

  The invention relates to the use of derivatives of 3-amidinophenylalanine as urokinase inhibitors for treating malignant tumors and the formation of metastases.

  该发明涉及利用3-酰胺基苯丙氨酸衍生物作为尿激酶抑制剂，用于治疗恶性肿瘤和转移瘤的形成。