二苯基2-哌啶基膦酸酯盐酸盐(1:1) | 174298-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 二苯基2-哌啶基膦酸酯盐酸盐(1:1)
• 英文名称: diphenyl piperidine-2-phosphonate hydrochloride
• 英文别名: Diphenyl piperidine-2-phosphonate hcl；2-diphenoxyphosphorylpiperidine;hydrochloride
• CAS: 174298-15-8
• 化学式: C₁₇H₂₀NO₃P*ClH
• mdl: MFCD00943528
• 分子量: 353.785
• InChiKey: DUBCYEVOEHZSNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.294
• 拓扑面积：
  47.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二苯基2-哌啶基膦酸酯盐酸盐(1:1) 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 22.25h， 生成 diphenyl lysylpiperidine-2-phosphonate dihydrochloride
  参考文献：
  名称：

  Dipeptide Phosphonates as Inhibitors of Dipeptidyl Peptidase IV

  摘要：

  A series of dipeptides which contained phosphonate analogs of proline and piperidine-2-carboxylic acid (homoproline) have been synthesized and tested as inhibitors of DPP-IV. The rates of inhibition of DPP-IV by these compounds are moderate, but the inhibitors are quite specific. The best inhibitor in the series is Ala-Pip(P)(OPh-4-Cl)(2) (13), which has a k(inact) of 0.353 s(-1) and K-I of 236 mu M. The DPP-IV inhibitors Ala-Pro(P)(OPh)(2) (6), Ala-Pro(P)(OPh-4-Cl)(2) (12), and Ala-Pip(P)(OPh-4-Cl)(2) (13) do not inhibit trypsin, human leukocyte elastase (HLE), porcine pancreatic elastase (PPE), adetylcholinesterase, papain, and cathepsin B. However, compounds 12 and 13 inhibited chymotrypsin slowly. Most of these dipeptides containing a homoproline phosphonate residue (Pip(P)) or a Pro phosphonate residue (pro(P)) at the P-1 site are stable in a pH 7.8 buffer with half-lives of several hours to several days. DPP-IV inhibited by 6, 7 (Ala-Pip(P)(OPh)(2)), 12, or 13 is quite stable, and no enzyme activity was recovered after removal of excess inhibitor and incubation buffer for 1 day. Since the phosphonate inhibitors are specific toward DPP-IV and the inhibited enzymes are stable, they should be useful in establishing the biological functions of DPP-IV and may be useful therapeutically in the prevention of the rejection of transplanted tissue.

  DOI：

  10.1021/jm00049a016

文献信息

• US5543396A
  申请人：——

  公开号：US5543396A

  公开（公告）日：1996-08-06
• [EN] PROLINE PHOSPHONATE DERIVATIVES<br/>[FR] DERIVES DE LA PROLINE PHOSPHONATE
  申请人：GEORGIA TECH RESEARCH CORPORATION

  公开号：WO1995029691A1

  公开（公告）日：1995-11-09

  (EN) Peptidyl derivatives of diesters of $g(a)-aminoalkylphosphonic acids, particularly those with proline or related structures, their use in inhibiting serine proteases with chymotrypsin-like, trypsin-like, elastase-like, and dipeptidyl peptidase IV specificity and their roles as anti-inflammatory agents, anticoagulants, anti-tumor agents, and anti-AIDS agents.(FR) L'invention traite de dérivés peptidyle de diesters d'acides $g(a)-aminoalkylphosphoniques, en particulier, ceux présentant une structure proline ou apparentée. L'invention concerne également leur utilisation pour inhiber des sérine protéases avec une spécificité apparentée à la chymotrypsine, à la trypsine, à l'élastase, et propre à la dipeptidyle peptidase IV et leur rôle comme agents anti-inflammatoires, anti-coagulants, anti-tumoraux et anti-SIDA.