(S)-1-(2-Cyclohexyl-2-oxo-acetyl)-pyrrolidine-2-carboxylic acid | 251949-22-1

• 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)-1-(2-Cyclohexyl-2-oxo-acetyl)-pyrrolidine-2-carboxylic acid
• 英文别名: (2S)-1-(2-cyclohexyl-2-oxoacetyl)pyrrolidine-2-carboxylic acid
• CAS: 251949-22-1
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: UGYSUYJFSVRTMG-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  3-苯基-1-丙烷硫醇 、 (S)-1-(2-Cyclohexyl-2-oxo-acetyl)-pyrrolidine-2-carboxylic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 3-phenyl-1-propyl (2S)-1-(2-cyclohexyl-1,2-dioxoethyl)-2-pyrrolidinecarbothioate
  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 (S)-1-(2-Cyclohexyl-2-oxo-acetyl)-pyrrolidine-2-carboxylic 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

• 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。
• 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。
• STEM-LIKE CELLS AND METHOD FOR REPROGRAMMING ADULT MAMMALIAN SOMATIC CELLS
  申请人：Weinstein David E.

  公开号：US20100317711A1

  公开（公告）日：2010-12-16

  A new use is provided for small molecule inhibitors of Oct4 and Sox 2 as a cellular reprogramming agent and a method of reprogramming adult mammalian somatic cells into stem-like cells is provided, using small molecule inhibitors of Oct4 and Sox 2 without the need of any material derived from embryos or fetuses, and without the need of potentially harmful transfecting vectors. Stem-like cells created by the present invention can be induced to differentiate into terminally differentiated adult somatic cells, such as, for example, neuronal cells.

  提供了一种新的用途，使用小分子抑制剂Oct4和Sox 2作为细胞重编程剂，提供了一种将成年哺乳动物体细胞重编程为类似干细胞的方法，使用Oct4和Sox 2的小分子抑制剂，无需使用任何来源于胚胎或胎儿的材料，也无需使用潜在有害的转染载体。本发明创建的类似干细胞可以诱导分化为终末分化的成年体细胞，例如神经元细胞。
• [EN] HAIR GROWTH COMPOSITIONS AND USES<br/>[FR] COMPOSITIONS POUR LA REPOUSSE DES CHEVEUX ET LEURS UTILISATIONS
  申请人：GUILFORD PHARMACEUTICALS INC.

  公开号：WO1998055090A1

  公开（公告）日：1998-12-10

  (EN) This invention relates to pharmaceutical compositions and methods for treating alopecia and promoting hair growth using non-immunosuppressive neuroimmunophilin FKBP ligands.(FR) L'invention concerne des compositions pharmaceutiques et des procédés pour traiter l'alopécie et favoriser la repousse des cheveux par le biais de ligands de protéines de liaison du FK (FKBP) avec des neuro-immunophillines du type non immunosuppresseur.

  这项发明涉及使用非免疫抑制神经免疫蛋白FKBP配体的药物组合物和治疗脱发以及促进头发生长的方法。