(2S)-1-[S-(benzyloxycarbonylmethyl)-N-(tert-butyloxycarbonyl)-L-cysteinyl]pyrrolidine-2-carbonitrile | 371247-88-0

• 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-(benzyloxycarbonylmethyl)-N-(tert-butyloxycarbonyl)-L-cysteinyl]pyrrolidine-2-carbonitrile
• 英文别名: benzyl 2-[(2R)-3-[(2S)-2-cyanopyrrolidin-1-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]sulfanylacetate
• CAS: 371247-88-0
• 化学式: C₂₂H₂₉N₃O₅S
• 分子量: 447.555
• InChiKey: XUTUXDQUPLYGTF-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  aqueous lithium hydroxide 、 (2S)-1-[S-(benzyloxycarbonylmethyl)-N-(tert-butyloxycarbonyl)-L-cysteinyl]pyrrolidine-2-carbonitrile 生成 (2S)-1-[N-(tert-butyloxycarbonyl)-S-(carboxymethyl)-L-cysteinyl]pyrrolidine-2-carbonitrile
  参考文献：
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• 作为产物：
  描述：

  pet 、 S-(benzyloxycarbonylmethyl)-N-(tert-butyloxycarbonyl)-L-cysteine 、 (S)-2-吡咯烷甲腈盐酸盐 生成 (2S)-1-[S-(benzyloxycarbonylmethyl)-N-(tert-butyloxycarbonyl)-L-cysteinyl]pyrrolidine-2-carbonitrile
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Inhibitors of dipeptidyl peptidase IV
  申请人：——

  公开号：US20030216450A1

  公开（公告）日：2003-11-20

  Compounds according to general formula (1), wherein R 1 is H or CN, X 1 is S, O, SO 2 or CH 2 , X 2 is O, S or CH 2 , X 3 is NR 5 or a carbonyl or thiocarbonyl group and R 4 is R 6 R 7 N, R 8 (CH 2 ) q OC(═O), R 8 (CH 2 ) q OC(═S), R 6 R 7 NC(═O), R 6 R 7 NC(═S); R 8 (CH 2 ) q C(═O), R 8 (CH 2 ) q C(═S) or R 8 (CH 2 ) q SO 2 , m is 1-3 and n is 0-4 are new. The compounds of the invention are inhibitors of dipeptidyl peptidase IV. Pharmaceutical compositions of the compounds of the invention, or pharmaceutically acceptable salts thereof, are useful in the treatment of,inter alia, type 2 diabetes.

  根据通用公式（1），化合物中R1为H或CN，X1为S、O、SO2或CH2，X2为O、S或CH2，X3为NR5或羰基或硫代羰基基团，R4为R6R7N、R8(CH2)qOC（═O）、R8(CH2)qOC（═S）、R6R7NC(═O)、R6R7NC(═S)；R8(CH2)qC(═O)、R8(CH2)qC(═S)或R8(CH2)qSO2，m为1-3，n为0-4的新化合物。该发明的化合物是二肽基肽酶IV的抑制剂。该发明的化合物的药用组合物或其药用盐在治疗2型糖尿病等疾病中有用。
• Novel dipeptidyl peptidase iv (dp-iv) inhibitors as anti-diabetic agents
  申请人：Evans M David

  公开号：US20050004205A1

  公开（公告）日：2005-01-06

  The present invention relates to a series of prodrugs of inhibitors of DP-IV with improved properties. The compounds can be used for the treatment of a number of human diseases, including impaired glucose tolerance and type II diabetes. The compounds of the invention are described by general formula (1); wherein R 1 is H or CN; R 2 is selected from CH 2 R 5 , CH 2 CH 2 R 5 and C(R 3 )(R 4 )—X 2 —(CH 2 ) a R 5 ; R 3 and R 4 are each independently selected from H and Me; R 5 is selected from CON(R 6 )(R 7 ), N(R 8 )C(=0)R 9 , N(R 8 )C(═S)R 9 , N(R 8 )SO 2 R 10 and N(R 8 )R 10 ; R 6 and R 7 are each independently R 11 (CH 2 ) b or together they are —(CH 2 ) 2 -Z-(CH 2 ) 2 — or CH 2 -o-C 6 H 4 -Z-CH 2 —; R 8 is H or Me; R 9 is selected from R 11 (CH 2 ) b , R 11 (CH 2 ) b O and N(R 6 )(R 7 ); R 10 is R 11 (CH 2 ) b ; R 11 is selected from H, alkyl, optionally substituted aryl, optionally substituted aroyl, optionally substituted arylsulphonyl and optionally substituted heteroaryl; R 12 is selected from H 2 NCH(R 13 )CO, H 2 NCH(R 14 )CONHCH(R 15 )CO, C(R 16 )═C(R 17 )COR 18 and R 19 OCO; R 13 , R 14 and R 15 are selected from the side chains of the proteinaceous amino acids; R 16 is selected from H, lower alkyl (C 1 -C 6 ) and phenyl; R 17 is selected from H and lower alkyl (C 1 -C 6 ); R 18 is selected from H, lower alkyl (C 1 -C 6 ), OH, O-(lower alkyl (C 1 -C 6 )) and phenyl; R 19 is selected from lower alkyl (C 1 -C 6 ), optionally substituted phenyl and R 20 C(=0)OC(R 21 )(R 22 ); R 20 , R 21 and R 22 are each independently selected from H and lower alkyl (C 1 -C 6 ); Z is selected from a covalent bond, —(CH 2 ) c —, —O—, —SO d — and —N(R 10 )—; X 1 is S or CH 2 ; X 2 is O, S or CH 2 ; a is 1, 2 or 3; b is 0-3; c is 1 or 2; and d is 0, 1 or 2.

  本发明涉及一系列具有改进性能的DP-IV抑制剂的前药。这些化合物可用于治疗多种人类疾病，包括糖耐量受损和2型糖尿病。该发明的化合物由通式（1）描述；其中，R1为H或CN；R2选自CH2R5，CH2CH2R5和C（R3）（R4）-X2-（CH2）aR5；R3和R4各自独立地选自H和Me；R5选自CON（R6）（R7），N（R8）C（=0）R9，N（R8）C（═S）R9，N（R8）SO2R10和N（R8）R10；R6和R7各自独立地为R11（CH2）b，或者它们为-（CH2）2-Z-（CH2）2-或CH2-o-C6H4-Z-CH2-；R8为H或Me；R9选自R11（CH2）b，R11（CH2）bO和N（R6）（R7）；R10选自R11（CH2）b；R11选自H，烷基，可选择取代的芳基，可选择取代的酰芳基，可选择取代的芳基磺酰基和可选择取代的杂环芳基；R12选自H2NCH（R13）CO，H2NCH（R14）CONHCH（R15）CO，C（R16）═C（R17）COR18和R19OCO；R13，R14和R15选自蛋白质氨基酸的侧链；R16选自H，低烷基（C1-C6）和苯基；R17选自H和低烷基（C1-C6）；R18选自H，低烷基（C1-C6），OH，O-（低烷基（C1-C6））和苯基；R19选自低烷基（C1-C6），可选择取代的苯基和R20C（=0）OC（R21）（R22）；R20，R21和R22各自独立地选自H和低烷基（C1-C6）；Z选自共价键，-（CH2）c-，-O-，-SOd-和-N（R10）-；X1为S或CH2；X2为O，S或CH2；a为1、2或3；b为0-3；c为1或2；d为0、1或2。
• INHIBITORS OF DIPEPTIDYL PEPTIDASE IV
  申请人：Ferring BV

  公开号：EP1282600A1

  公开（公告）日：2003-02-12
• US7144886B2
  申请人：——

  公开号：US7144886B2

  公开（公告）日：2006-12-05
• US7189728B2
  申请人：——

  公开号：US7189728B2

  公开（公告）日：2007-03-13