(2S)-1-(N'-(methoxycarbonyl)isoleucyl)pyrrolidine-2-carbonitrile | 341997-64-6

• 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-(N'-(methoxycarbonyl)isoleucyl)pyrrolidine-2-carbonitrile
• 英文别名: methyl N-[(2S,3S)-1-[(2S)-2-cyanopyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamate
• CAS: 341997-64-6
• 化学式: C₁₃H₂₁N₃O₃
• 分子量: 267.328
• InChiKey: GFOOZNGTAHFZJL-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S)-1-(isoleucyl)pyrrolidine-2-carbonitrile hydrochloride 、 氯甲酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 (2S)-1-(N'-(methoxycarbonyl)isoleucyl)pyrrolidine-2-carbonitrile
  参考文献：
  名称：

  Novel antidiabetic agents

  摘要：

  根据一般式（1），1-（2'-氨基酰基）-2-氰基吡咯烷衍生物化合物是治疗糖耐量受损或2型糖尿病的DP-IV抑制剂；其中A选自2、3和4组；X选自与天然氨基酸相对应的氨基酰基、酰基R3CO、基团R4COOC（R5）（R6）OCO、甲氧羰基、乙氧羰基和苄氧羰基；R1选自H、C1-C6烷基残基、（CH2）aNHW1、（CH2）bCOW2、（CH2）cOW3、CH（Me）OW4、（CH2）d-C6H4-W5和（CH2）eSW6，其中a为2-5，b为1-4，c为1-2，d为1-2，e为1-3，W1为COW6，CO2W6或SO2W6，W2为OH、NH2、OW6或NHW6，W3为H或W6，W4为H或W6，W5为H、OH或OMe，W6为C1-C6烷基、可选取代苯基、可选取代杂环基或苄基，R2选自H和（CH2）n-C5H3N-Y，其中n为2-4，Y为H、F、Cl、NO2或CN，或R1和R2一起为—（CH2）p-，其中p为3或4；R3选自H、C1-C6烷基和苯基；R4选自H、C1-C6烷基、苄基和可选取代苯基；R5和R6各自独立地选自H和C1-C6烷基，或一起为—（CH2）m—，其中m为4-6；R7选自吡啶基和可选取代苯基；R8选自H和C1-C3烷基；R9选自H、C1-C6烷基、C1-C6烷氧基和苯基。

  公开号：

  US20030096857A1

文献信息

• Antidiabetic agents
  申请人：Ferring BV

  公开号：US07169806B2

  公开（公告）日：2007-01-30

  Compounds which are 1-(2′-aminoacyl)-2-cyanopyrrolidine derivatives according to general formula (1) are DP-IV inhibitors for treatment of impaired glucose tolerance or type 2 diabetes; wherein A is selected from groups (2, 3 and 4); X is selected from aminoacyl groups corresponding to the natural amino acids, acyl groups R3CO, groups R4COOC(R5)(R6)OCO, methoxycarbonyl, ethoxycarbonyl and benzyloxycarbonyl; R1 is selected from H, C1–C6alkyl residues, (CH2)aNHW1, (CH2)bCOW2, (CH2)cOW3, CH(Me)OW4, (CH2)d—C6H4—W5 and (CH2)eSW6, where a is 2–5, b is 1–4, c is 1–2, d is 1–2, e is 1–3, W1 is COW6, CO2W6 or SO2W6, W2 is OH, NH2, OW6 or NHW6, W3 is H or W6, W4 is H or W6, W5 is H, OH or OMe, and W6 is C1–C6 alkyl, optionally substituted phenyl, optionally substituted heteroaryl or benzyl and R2 is selected from H and (CH2)n—C5H3N—Y, where n is 2–4 and Y is H, F, Cl, NO2 or CN, or R1 and R2 together are —(CH2)p— where p is 3 or 4; R3 is selected from H, C1–C6 alkyl and phenyl; R4 is selected from H, C1–C6 alkyl, benzyl and optionally substitued phenyl; R5 and R6 are each independently selected from H and C1–C6 alkyl or together are —(CH2)m—, where m is 4–6; R7 is selected from pyridyl and optionally substituted phenyl; R8 is selected from H and C1–C3 alkyl; and R9 is selected from H, C1–C6 alkyl, C1–C6 alkoxy and phenyl.

  根据通式（1），1-（2'-氨基酰基）-2-氰基吡咯烷衍生物化合物是治疗糖耐量受损或2型糖尿病的DP-IV抑制剂。其中，A选择自组（2、3和4）；X选择自然氨基酸对应的氨基酰基，酰基R3CO，组R4COOC（R5）（R6）OCO，甲氧羰基，乙氧羰基和苄氧羰基；R1选择自H、C1-C6烷基残基、（CH2）aNHW1、（CH2）bCOW2、（CH2）cOW3、CH（Me）OW4、（CH2）d-C6H4-W5和（CH2）eSW6，其中a为2-5，b为1-4，c为1-2，d为1-2，e为1-3，W1为COW6，CO2W6或SO2W6，W2为OH、NH2、OW6或NHW6，W3为H或W6，W4为H或W6，W5为H、OH或OMe，W6为C1-C6烷基、可选取代苯基、可选取代杂环基或苄基，R2选择自H和（CH2）n-C5H3N-Y，其中n为2-4，Y为H、F、Cl、NO2或CN，或R1和R2共同为-（CH2）p-，其中p为3或4；R3选择自H、C1-C6烷基和苯基；R4选择自H、C1-C6烷基、苄基和可选取代苯基；R5和R6各自选择自H和C1-C6烷基或共同为-（CH2）m-，其中m为4-6；R7选择自吡啶基和可选取代苯基；R8选择自H和C1-C3烷基；R9选择自H、C1-C6烷基、C1-C6烷氧基和苯基。
• N-SUBSTITUTED 2-CYANOPYRROLIDINES AND THEIR USE AS ANTIDIABETIC AGENTS
  申请人：Ferring BV

  公开号：EP1351932A2

  公开（公告）日：2003-10-15
• US6911467B2
  申请人：——

  公开号：US6911467B2

  公开（公告）日：2005-06-28
• US7169806B2
  申请人：——

  公开号：US7169806B2

  公开（公告）日：2007-01-30
• [EN] NOVEL ANTIDIABETIC AGENTS<br/>[FR] NOUVEAUX AGENTS ANTIDIABETIQUES
  申请人：FERRING BV

  公开号：WO2001040180A2

  公开（公告）日：2001-06-07

  Compounds which are 1-(2'-aminoacyl)-2-cyanopyrrolidine derivatives according to general formula (1) are DP-IV inhibitors for treatment of impaired glucose tolerance or type 2 diabetes; wherein A is selected from groups (2, 3 and 4); X is selected from aminoacyl groups corresponding to the natural amino acids, acyl groups R3CO, groups R?4COOC(R5)(R6¿)OCO, methoxycarbonyl, ethoxycarbonyl and benzyloxycarbonyl; R1 is selected from H, C¿1?-C6 alkyl residues, (CH2)aNHW?1, (CH¿2)bCOW2, (CH2)cOW3, CH(Me)OW4, (CH2)d-C6H4-W5 and (CH¿2)eSW?6, where a is 2-5, b is 1-4, c is 1-2, d is 1-2, e is 1-3, W?1 is COW6, CO¿2W6 or SO¿2W?6, W2 is OH, NH¿2?, OW?6 or NHW6, W3¿ is H or W6, W4 is H or W6, W5 is H, OH or OMe, and W6 is C1-C6 alkyl, optionally substituted phenyl, optionally substituted heteroaryl or benzyl and R2 is selected from H and (CH¿2?)n-C5H3N-Y, where n is 2-4 and Y is H, F, Cl, NO2 or CN, or R?1 and R2¿ together are -(CH¿2?)p-where p is 3 or 4; R?3¿ is selected from H, C¿1?-C6 alkyl and phenyl; R?4¿ is selected from H, C¿1?-C6 alkyl, benzyl and optionally substitued phenyl; R?5 and R6¿ are each independently selected from H and C¿1?-C6 alkyl or together are -(CH2)m-, where m is 4-6; R?7¿ is selected from pyridyl and optionally substituted phenyl; R8 is selected from H and C¿1?-C3 alkyl; and R?9¿ is selected from H, C¿1?-C6 alkyl, C1-C6 alkoxy and phenyl.