2-carboxy-alpha-(3-mercaptopropyl)-benzenepropanoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-carboxy-alpha-(3-mercaptopropyl)-benzenepropanoic acid
• 英文别名: 2-[2-Carboxy-2-(3-sulfanylpropyl)ethyl]benzoic acid；2-(2-carboxy-5-sulfanylpentyl)benzoic acid
• 化学式: C₁₃H₁₆O₄S
• 分子量: 268.334
• InChiKey: AJRYUIBEXXWDCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴甲基苯甲酸甲酯 在 sodium hydroxide 、 三异丙基硅烷 、 苄基三乙基氯化铵 、 potassium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 11.83h， 生成 2-carboxy-alpha-(3-mercaptopropyl)-benzenepropanoic acid
  参考文献：
  名称：

  通过修饰P1'侧链优化基于巯基的谷氨酸羧肽酶II抑制剂的结构。

  摘要：

  已经合成了一系列在P1'位置含有苄基部分的基于硫醇的抑制剂，并测试了它们抑制谷氨酸羧肽酶II（GCP II）的能力。发现3-（2-羧基-5-巯基戊基）苯甲酸6c是最有效的抑制剂，IC（50）值为15 nM，比2-（3-巯基丙基）戊二酸的效力高6倍（2 -MPPA），一种先前发现的口服活性GCP II抑制剂。随后的SAR研究表明，6c，3-（1-羧基-4-巯基丁氧基）苯甲酸26a和3-[（1-羧基-4-巯基丁基）硫代]苯甲酸26b的苯氧基和苯硫烷基类似物也具有很强的效力。对GCP II的抑制活性。在神经性疼痛的大鼠慢性收缩损伤（CCI）模型中，化合物6c和26a口服后可明显减少痛觉过敏（1。

  DOI：

  10.1021/jm051019l

文献信息

• Thiol-based NAALADase inhibitors
  申请人：GUILFORD PHARMACEUTICALS INC.

  公开号：US20030105088A1

  公开（公告）日：2003-06-05

  This invention relates to new compounds, pharmaceutical compositions and diagnostic kits comprising such compounds, and methods of using such compounds for inhibiting NAALADase enzyme activity, detecting diseases where NAALADase levels are altered, effecting neuronal activity, effecting TGF-&bgr; activity, inhibiting angiogenesis, and treating glutamate abnormalities, diabetic neuropathy, pain, compulsive disorders, prostate diseases, cancers and glaucoma.

  本发明涉及新化合物、制药组合物和诊断试剂盒，所述化合物包括在内，以及使用这些化合物抑制NAALADase酶活性、检测NAALADase水平发生变化的疾病、影响神经元活动、影响TGF-&bgr;活性、抑制血管生成和治疗谷氨酸异常、糖尿病神经病变、疼痛、强迫性障碍、前列腺疾病、癌症和青光眼的方法。
• THIOL-BASED NAALADASE INHIBITORS
  申请人：GUILFORD PHARMACEUTICALS INC.

  公开号：EP1353903A2

  公开（公告）日：2003-10-22
• Compounds which bind PSMA and uses thereof
  申请人：Heston Warren D.W.

  公开号：US20080311037A1

  公开（公告）日：2008-12-18

  A compound is represented by Structural Formula A1: C—B-L-A  A1 or a pharmaceutically acceptable salt or solvate thereof. A is a prostate specific membrane antigen (PSMA) ligand; L is an optionally substituted aliphatic or heteroaliphatic linking group; B includes at least one optionally substituted moiety selected from the group consisting of a sugar, a charged group, an aryl ring, and a heteroaryl ring, wherein B optionally includes a drug or a labeling agent; and C is H, a drug, or a labeling agent, wherein CB together comprises the drug or the labeling agent. The compounds are useful as PSMA agents and in pharmaceutical compositions, methods for treating and detecting diseases such as cancer in a subject, methods for identifying cancer cells in a sample, methods for inhibiting tumor neovascularization, methods for identifying drugs that can treat cancer, and the like.
• US6992215B2
  申请人：——

  公开号：US6992215B2

  公开（公告）日：2006-01-31
• [EN] THIOL-BASED NAALADASE INHIBITORS<br/>[FR] INHIBITEURS DE NAALADASE A BASE DE THIOL
  申请人：GUILFORD PHARM INC

  公开号：WO2002057222A2

  公开（公告）日：2002-07-25

  This invention relates to thiol compounds of the formulae I, II or III (in which the variables are as defined in the claims), pharmaceutical compositions and diagnostic kits comprising such compounds and methods of using such compounds for inhibiting NAALADase enzyme activity, detecting diseases where NAALADase levels are altered, effecting neuronal activity, effecting TGF-β activity, inhibiting angiogenesis, and treating glutamate abnormalities, diabetic neuropathy, pain, compulsive disorders, prostate diseases, cancers and glaucoma.