3-hydroxyamidinophenylacetic acid | 1251460-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-hydroxyamidinophenylacetic acid
• 英文别名: 2-[3-[(Z)-N'-hydroxycarbamimidoyl]phenyl]acetic acid
• CAS: 1251460-52-2
• 化学式: C₉H₁₀N₂O₃
• 分子量: 194.19
• InChiKey: AGKGAIJRFDGTEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxyamidinophenylacetic acid 在 palladium 10% on activated carbon 、 氢气 、 盐酸 作用下， 以 水 为溶剂， 50.0 ℃ 、344.75 kPa 条件下， 反应 18.0h， 以90%的产率得到3-amidinophenylacetic acid hydrochloride
  参考文献：
  名称：

  Conformationally restricted analogs of the direct thrombin inhibitor FM 19

  摘要：

  The serine protease thrombin plays several key roles in the clotting cascade within the hemostatic system, such as in fibrin formation and platelet activation. Thus, development of an inhibitor that binds to the enzyme's active site (a direct thrombin inhibitor) offers an approach for the treatment of thrombus-associated diseases. Previous structure-activity relationship studies originally based on the bradykinin breakdown product Arg-Pro-Pro-Gly-Phe (RPPGF) led to the development of lead compound FM 19 (D-Arg-Oic-Pro-D-Ala-Phe(p-Me)-NH2). The recently determined X-ray structure of FM 19 in the active site of thrombin has revealed sites of modification to potentially improve inhibition. In this study, we report the synthesis and biological characterization of nine peptides that replace only the D-Arg residue of the FM 19 sequence, investigating ways to add conformational restriction, modification of the basic moiety at the end of the side chain, and removal of the charge from the N-terminus. Two of these peptides, 6 and 7 (IC50 values of 0.51 and 0.45 mu M, respectively), show similar potency to the best compounds in the FM 19 series reported thus far. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.045
• 作为产物：
  描述：

  3-氰基-苯乙酸 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以50%的产率得到3-hydroxyamidinophenylacetic acid
  参考文献：
  名称：

  Conformationally restricted analogs of the direct thrombin inhibitor FM 19

  摘要：

  The serine protease thrombin plays several key roles in the clotting cascade within the hemostatic system, such as in fibrin formation and platelet activation. Thus, development of an inhibitor that binds to the enzyme's active site (a direct thrombin inhibitor) offers an approach for the treatment of thrombus-associated diseases. Previous structure-activity relationship studies originally based on the bradykinin breakdown product Arg-Pro-Pro-Gly-Phe (RPPGF) led to the development of lead compound FM 19 (D-Arg-Oic-Pro-D-Ala-Phe(p-Me)-NH2). The recently determined X-ray structure of FM 19 in the active site of thrombin has revealed sites of modification to potentially improve inhibition. In this study, we report the synthesis and biological characterization of nine peptides that replace only the D-Arg residue of the FM 19 sequence, investigating ways to add conformational restriction, modification of the basic moiety at the end of the side chain, and removal of the charge from the N-terminus. Two of these peptides, 6 and 7 (IC50 values of 0.51 and 0.45 mu M, respectively), show similar potency to the best compounds in the FM 19 series reported thus far. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.045

文献信息

• [EN] OXADIAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXADIAZOLE
  申请人：MERCK SERONO SA

  公开号：WO2010112461A1

  公开（公告）日：2010-10-07

  The invention relates to compounds of formula (I); wherein R1, R2, Ra, Rb, W, Q and S have the meanings given in claim 1. The compounds are useful e.g. in the treatment of autoimmune disorders, such as multiple sclerosis.

  该发明涉及化合物的公式(I)；其中R1、R2、Ra、Rb、W、Q和S具有权利要求1中给定的含义。这些化合物在治疗自身免疫性疾病，如多发性硬化症等方面是有用的。
• OXADIAZOLE DERIVATIVES
  申请人：Quattropani Anna

  公开号：US20120035226A1

  公开（公告）日：2012-02-09

  The invention relates to oxadiazole compounds of formula I. The compounds are useful e.g. in the treatment of autoimmune disorders, such as multiple sclerosis.

  本发明涉及式I的噁唑烷化合物。这些化合物在治疗自身免疫性疾病（例如多发性硬化症）方面是有用的。
• US8815919B2
  申请人：——

  公开号：US8815919B2

  公开（公告）日：2014-08-26
• US8802704B2
  申请人：——

  公开号：US8802704B2

  公开（公告）日：2014-08-12
• Conformationally restricted analogs of the direct thrombin inhibitor FM 19
  作者：Elizabeth A. Girnys、Vanessa R. Porter、Henry I. Mosberg

  DOI：10.1016/j.bmc.2011.10.045

  日期：2011.12

  The serine protease thrombin plays several key roles in the clotting cascade within the hemostatic system, such as in fibrin formation and platelet activation. Thus, development of an inhibitor that binds to the enzyme's active site (a direct thrombin inhibitor) offers an approach for the treatment of thrombus-associated diseases. Previous structure-activity relationship studies originally based on the bradykinin breakdown product Arg-Pro-Pro-Gly-Phe (RPPGF) led to the development of lead compound FM 19 (D-Arg-Oic-Pro-D-Ala-Phe(p-Me)-NH2). The recently determined X-ray structure of FM 19 in the active site of thrombin has revealed sites of modification to potentially improve inhibition. In this study, we report the synthesis and biological characterization of nine peptides that replace only the D-Arg residue of the FM 19 sequence, investigating ways to add conformational restriction, modification of the basic moiety at the end of the side chain, and removal of the charge from the N-terminus. Two of these peptides, 6 and 7 (IC50 values of 0.51 and 0.45 mu M, respectively), show similar potency to the best compounds in the FM 19 series reported thus far. (C) 2011 Elsevier Ltd. All rights reserved.