N-<(tert-butyloxy)carbonyl>-trans-3-n-propyl-L-proline | 123724-22-1

• 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: N-<(tert-butyloxy)carbonyl>-trans-3-n-propyl-L-proline
• 英文别名: (2S,3S)-N-(tert-butyloxycarbonyl)-3-n-propylproline；Boc-3PP-OH；(2S,3S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-3-propylpyrrolidine-2-carboxylic acid
• CAS: 123724-22-1
• 化学式: C₁₃H₂₃NO₄
• 分子量: 257.33
• InChiKey: KYXWFNMTPBXNNV-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<(tert-butyloxy)carbonyl>-trans-3-n-propyl-L-proline 在 N-甲基吗啉 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.1h， 生成 Boc-3PP-Asp(OBn)-(N-Me)Phe-NH2
  参考文献：
  名称：

  Synthesis and biological activity of CCK heptapeptide analogs. Effects of conformational constraints and standard modifications on receptor subtype selectivity, functional activity in vitro, and appetite suppression in vivo

  摘要：

  A series of modifications of the CCK7 analogue (des-NH2)Tyr(SO3-)-Nle-Gly-Trp-Nle-Asp-Phe-NH2 was prepared and tested for binding to guinea pig CCK-A and CCK-B receptors and in CCK-A-mediated functional assays. Selected analogues also were tested for appetite suppressant activity in rats. Several conformationally restricted residues in the C-terminal tetrapeptide region, including DELTA(Z)-Phe33, (N-Me)Phe33, (N-Me)Asp32, (N-Me)Leu31, and 3PP31 (3PP = trans-3-n-propyl-L-proline) were found to be acceptable modifications at one or both receptor subtypes. The (N-Me)Asp32 and (N-Me)Leu31 modifications afforded potent and selective CCK-A and CCK-B ligands, respectively. SAR studies in the N-terminal acyldipeptide region examined structural requirements for the side chain at position 28, where Gly and Pro replacements were found to possess high affinity at both receptor subtypes. Other conformationally restrictive modifications were less active. All of the analogues that showed high affinity (<10 nM) for the CCK-A receptor also were full agonists in amylase release and most were full or nearly full agonists in the phosphoinositide (PI) turnover assay, the most notable exception being the DELTA(Z)-Phe33 analogue, which showed 69% of the maximal response in the PI assay. Potent activity in suppression of food intake in rats was found for selected analogues.

  DOI：

  10.1021/jm00094a001
• 作为产物：
  描述：

  (2R)-1-(tert-butyloxycarbonyl)-2-<<(2-tetrahydropyranyl)oxy>methyl>-3-(phenylsulfonyl)pyrrolidine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 N-<(tert-butyloxy)carbonyl>-trans-3-n-propyl-L-proline
  参考文献：
  名称：

  光学纯的顺式和反式3-取代脯氨酸衍生物的新型立体发散性合成。

  摘要：

  DOI：

  10.1021/jo961790r

文献信息

• Tetrapeptide type-B CCK receptor ligands
  申请人：ABBOTT LABORATORIES

  公开号：EP0405506A1

  公开（公告）日：1991-01-02

  A tetrapeptide type-B CCK receptor ligand of the formula A-B-C-D or a pharmaceutically acceptable salt thereof, which is useful for treating central nervous system disorders, substance abuse, gastrointestinal disorders, endocrine disorders, eating-related disorders and treatment of shock, respiratory and cardiocirculatory insufficiencies.

  式中的四肽-B 型 CCK 受体配体 A-B-C-D 或其药学上可接受的盐，可用于治疗中枢神经系统疾病、药物滥用、胃肠功能紊乱、内分泌失调、进食相关疾病以及休克、呼吸和心血管功能不全的治疗。
• Conformationally constrained amino acids. Synthesis and optical resolution of 3-substituted proline derivatives
  作者：John Y. L. Chung、James T. Wasicak、William A. Arnold、Catherine S. May、Alex M. Nadzan、Mark W. Holladay

  DOI：10.1021/jo00288a045

  日期：1990.1
• CHUNG, JOHN Y. L.;WASICAK, JAMES T.;ARNOLD, WILLIAM A.;MAY, CATHERINE S.;+, J. ORG. CHEM., 55,(1990) N, C. 270-275
  作者：CHUNG, JOHN Y. L.、WASICAK, JAMES T.、ARNOLD, WILLIAM A.、MAY, CATHERINE S.、+

  DOI：——

  日期：——
• trans-3-n-propyl-L-proline is a highly favorable, conformationally restricted replacement for methionine in the C-terminal tetrapeptide of cholecystokinin. Stereoselective synthesis of 3-allyl- and 3-n-propyl-L-proline derivatives from 4-hydroxy-L-proline
  作者：Mark W. Holladay、Chun Wel Lin、Catherine S. May、David S. Garvey、David G. Witte、Thomas R. Miller、Caroline A. W. Wolfram、Alex M. Nadzan

  DOI：10.1021/jm00105a068

  日期：1991.1
• US5340802A
  申请人：——

  公开号：US5340802A

  公开（公告）日：1994-08-23