(2S)-1-(S'-tert-butyl-N'-(ethyloxycarbonyl)cysteinyl)pyrrolidine-2-carbonitrile | 341997-77-1

• 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: (2S)-1-(S'-tert-butyl-N'-(ethyloxycarbonyl)cysteinyl)pyrrolidine-2-carbonitrile
• 英文别名: ethyl N-[(2R)-3-tert-butylsulfanyl-1-[(2S)-2-cyanopyrrolidin-1-yl]-1-oxopropan-2-yl]carbamate
• CAS: 341997-77-1
• 化学式: C₁₅H₂₅N₃O₃S
• 分子量: 327.448
• InChiKey: KHYRWVOJYGLCFS-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S)-1-(S'-tert-butylcysteinyl)pyrrolidine-2-carbonitrile trifluoroacetate 、 氯甲酸乙酯 、 三乙胺 在 potassium hydrogensulfate 、 碳酸氢钠 、 水 、 Brine 、 Sodium sulfate-III 、 乙酸乙酯 、 Pet. Ether 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (2S)-1-(S'-tert-butyl-N'-(ethyloxycarbonyl)cysteinyl)pyrrolidine-2-carbonitrile
  参考文献：
  名称：

  Antidiabetic agents

  摘要：

  通式（1）所示的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选自对应于天然氨基酸的氨基酰基、酰基R3CO、羧酸酯基团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，或者一起为—(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：

  US06911467B2

文献信息

• Novel antidiabetic agents
  申请人：——

  公开号：US20030096857A1

  公开（公告）日：2003-05-22

  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 R 3 CO, groups R 4 COOC(R 5 )(R 6 )OCO, methoxycarbonyl, ethoxycarbonyl and benzyloxycarbonyl; R 1 is selected from H, C 1 -C 6 alkyl residues, (CH 2 ) a NHW 1 , (CH 2 ) b COW 2 , (CH 2 ) c OW 3 , CH(Me)OW 4 , (CH 2 ) d —C 6 H 4 —W 5 and (CH 2 ) e SW 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 COW 6 , CO 2 W 6 or SO 2 W 6 , W 2 is OH, NH 2 , OW 6 or NHW 6 , W 3 is H or W 6 , W 4 is H or W 6 , W 5 is H, OH or OMe, and W 6 is C 1 -C 6 alkyl, optionally substituted phenyl, optionally substituted heteroaryl or benzyl and R 2 is selected from H and (CH 2 ) n —C 5 H 3 N—Y, where n is 2-4 and Y is H, F, Cl, NO 2 or CN, or R 1 and R 2 together are —(CH 2 ) p -where p is 3 or 4; R 3 is selected from H, C 1 -C 6 alkyl and phenyl; R 4 is selected from H, C 1 -C 6 alkyl, benzyl and optionally substitued phenyl; R 5 and R 6 are each independently selected from H and C 1 -C 6 alkyl or together are —(CH 2 ) m —, where m is 4-6; R 7 is selected from pyridyl and optionally substituted phenyl; R 8 is selected from H and C 1 -C 3 alkyl; and R 9 is selected from H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and phenyl.

  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。
• 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.