(2S)-1-(1,2-dioxo-3,3-dimethylbutyl)-2-pyrrolidinecarboxylic acid | 251949-17-4

• 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: (2S)-1-(1,2-dioxo-3,3-dimethylbutyl)-2-pyrrolidinecarboxylic acid
• 英文别名: (2S)-1-(3,3-dimethyl-2-oxobutanoyl)pyrrolidine-2-carboxylic acid
• CAS: 251949-17-4
• 化学式: C₁₁H₁₇NO₄
• 分子量: 227.26
• InChiKey: GXNVEJUXPYTIGP-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-1-(1,2-dioxo-3,3-dimethylbutyl)-2-pyrrolidinecarboxylic acid 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成 (S)-1-(3,3-Dimethyl-2-oxo-butyryl)-pyrrolidine-2-carboxylic acid (3-phenyl-propyl)-amide
  参考文献：
  名称：

  Synthesis of N-Glyoxyl Prolyl and Pipecolyl Amides and Thioesters and Evaluation of Their In Vitro and In Vivo Nerve Regenerative Effects

  摘要：

  The recent discovery that small molecule ligands for the peptidyl-prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these compounds are independent of the immunosuppressive pathways by which drugs such as FK506 and rapamycin operate. Previous work by ourselves and other groups exploring the structure-activity relationships (SAR) of small molecules that mimic only the FKBP binding domain portion of FK506 has focused on esters of proline and pipecolic acid. We have explored amide and thioester analogues of these earlier structures and found that they too are extremely potent in promoting recovery of lesioned dopaminergic pathways in a mouse model of Parkinson's disease. Several compounds were shown to be highly effective upon oral administration after lesioning of the dopaminergic pathway, providing further evidence of the potential clinical utility of a variety of structural classes of FKBP12 ligands.

  DOI：

  10.1021/jm010556c
• 作为产物：
  描述：

  methyl (2S)-1-(1,2-dioxo-2-methoxyethyl)-2-pyrrolidinecarboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 (2S)-1-(1,2-dioxo-3,3-dimethylbutyl)-2-pyrrolidinecarboxylic acid
  参考文献：
  名称：

  Synthesis of N-Glyoxyl Prolyl and Pipecolyl Amides and Thioesters and Evaluation of Their In Vitro and In Vivo Nerve Regenerative Effects

  摘要：

  The recent discovery that small molecule ligands for the peptidyl-prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these compounds are independent of the immunosuppressive pathways by which drugs such as FK506 and rapamycin operate. Previous work by ourselves and other groups exploring the structure-activity relationships (SAR) of small molecules that mimic only the FKBP binding domain portion of FK506 has focused on esters of proline and pipecolic acid. We have explored amide and thioester analogues of these earlier structures and found that they too are extremely potent in promoting recovery of lesioned dopaminergic pathways in a mouse model of Parkinson's disease. Several compounds were shown to be highly effective upon oral administration after lesioning of the dopaminergic pathway, providing further evidence of the potential clinical utility of a variety of structural classes of FKBP12 ligands.

  DOI：

  10.1021/jm010556c

文献信息

• Rotamase enzyme activity inhibitors
  申请人：——

  公开号：US20020052410A1

  公开（公告）日：2002-05-02

  This invention relates to methods of using neurotrophic compounds having an affinity for FKBP-type immunophilins to stimulate or promote neuronal growth or regeneration and to prevent neuronal degeneration.

  这项发明涉及使用对FKBP型免疫蛋白亲和力较高的神经营养因子化合物的方法，以刺激或促进神经细胞的生长或再生，并防止神经细胞的退化。
• Pyrrolidine derivative hair growth compositions and uses
  申请人：GPL NIL Holdings, Inc.,

  公开号：US20010049381A1

  公开（公告）日：2001-12-06

  This invention relates to pharmaceutical compositions and methods for treating alopecia and promoting hair growth using pyrrolidine derivatives.

  这项发明涉及使用吡咯烷衍生物治疗脱发并促进头发生长的药物组合物和方法。
• N-oxide of heterocyclic ester, amide, thioester, or ketone hair growth compositions and uses
  申请人：GPI NIL Holdings, Inc.

  公开号：US20020065297A1

  公开（公告）日：2002-05-30

  This invention relates to pharmaceutical compositions and methods for treating alopecia and promoting hair growth using an N-oxide of a heterocyclic ester, amide, thioester, or ketone.

  这项发明涉及使用杂环酯、酰胺、硫酯或酮的N-氧化物治疗脱发和促进头发生长的药物组合物和方法。
• Neurotrophic pyrrolidines and piperidines, and related compositions and methods
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：US06809107B1

  公开（公告）日：2004-10-26

  This invention provides compounds having the following general structures: This invention also provides pharmaceutical compositions comprising same and methods of using these compositions to treat and prevent disorders characterized by neuronal damage.

  这项发明提供具有以下一般结构的化合物：这项发明还提供包含相同化合物的药物组合物，以及使用这些组合物治疗和预防由神经元损伤所特征化的疾病的方法。
• Method for treating nerve injury caused as a result of surgery
  申请人：——

  公开号：US20030203890A1

  公开（公告）日：2003-10-30

  The present invention relates generally to methods for treating or preventing nerve injury in a warm-blooded animal caused as a consequence of surgery by administering neurotrophic compounds described below. The invention relates more specifically to methods for treating or preventing nerve injury caused as a consequence of prostate surgery as well as erectile dysfunction.

  本发明一般涉及通过给予下文描述的神经营养化合物来治疗或预防温血动物因手术而引起的神经损伤的方法。该发明更具体地涉及治疗或预防由前列腺手术以及勃起功能障碍引起的神经损伤的方法。