(2S,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl ester | 77345-53-0

• 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,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl ester
• 英文别名: cis-1-benzyloxycarbonyl-4-(toluene-4-sulfonyloxy)-L-proline-methyl ester；cis-1-Benzyloxycarbonyl-4-(toluol-4-sulfonyloxy)-L-prolin-methylester；(2S,4S)-1-Benzyl 2-methyl 4-(tosyloxy)pyrrolidine-1,2-dicarboxylate；1-O-benzyl 2-O-methyl (2S,4S)-4-(4-methylphenyl)sulfonyloxypyrrolidine-1,2-dicarboxylate
• CAS: 77345-53-0
• 化学式: C₂₁H₂₃NO₇S
• 分子量: 433.482
• InChiKey: CRGZVZQOSILHGM-HKUYNNGSSA-N

物化性质

• 沸点：
  579.0±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl ester 在 盐酸 、 sodium hydroxide 、 sodium 作用下， 以 溶剂黄146 为溶剂， 反应 47.0h， 生成 trans-4-(phenylthio)-L-proline methyl ester monohydrochloride
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines

  摘要：

  Analogues of captopril, enalaprilat, and the phosphinic acid [hydroxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline incorporating 4-substituted proline derivatives have been synthesized and evaluated as inhibitors of angiotensin-converting enzyme (ACE) in vitro and in vivo. The 4-substituted prolines, incorporating alkyl, aryl, alkoxy, aryloxy, alkylthio, and arylthio substituents were prepared from derivatives of 4-hydroxy- and 4-ketoproline. In general, analogues of all three classes of inhibitors with hydrophobic substituents on proline were more potent in vitro than the corresponding unsubstituted proline compounds. 4-Substituted analogues of captopril showed greater potency and duration of action than the parent compound as inhibitors of the angiotensin I induced pressor response in normotensive rats. The S-benzoyl derivative of cis-4-(phenylthio)captopril, zofenopril, was found to be one of the most potent compounds of this class and is now being evaluated clinically as an antihypertensive agent. In the phosphinic acid series, the 4-ethylenethioketal and trans-4-cyclohexyl derivatives were found to be the most potent compounds in vitro and in vivo. A prodrug of the latter compound, fosinopril, is also being evaluated in clinical trials.

  DOI：

  10.1021/jm00401a014
• 作为产物：
  描述：

  L-羟基脯氨酸 在 氯化亚砜 、 偶氮二甲酸二异丙酯 、 碳酸氢钠 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (2S,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl ester
  参考文献：
  名称：

  Two prolines with a difference: contrasting stereoelectronic effects of 4R/S-aminoproline on triplex stability in collagen peptides [Pro(X)-Pro(Y)-Gly]nElectronic supplementary information (ESI) available: 1H NMR spectra and coupling constant analysis of 3 and 4; synthetic schemes for 3, 4, 5 and 6; FABMS of 3 and 4; MALDI-TOF MS of 5 and 6; HPLC of peptides 5 and 6. See http://www.rsc.org/suppdata/cc/b3/b308581c/

  摘要：

  在胶原肽[pro(X)-pro(Y)-Gly]n中，当4R/S-氨基脯氨酸位于X位置时，对三重螺旋稳定性表现出pH和立体化学依赖性效应。

  DOI：

  10.1039/b308581c

文献信息

• Chimeric (aeg-pyrrolidine)PNAs: synthesis and stereo-discriminative duplex binding with DNA/RNA
  作者：Pallavi S. Lonkar、Krishna N. Ganesh、Vaijayanti A. Kumar

  DOI：10.1039/b407292h

  日期：——

  The design and facile conversion of naturally occurring 4-hydroxyproline to all four diastereomers of thymine pyrrolidine PNA monomer, (2R,4S)-adenine, -guanine and -cytosine monomers and their incorporation into duplex forming PNA oligomers is reported. The interesting results of the hybridization studies with complementary DNA/RNA sequences in either parallel or antiparallel orientation reveal the stereochemistry-dependent DNA vs. RNA discriminations and parallel/antiparallel orientation selectivity.

  报道了天然存在的4-羟基脯氨酸的设计及其方便转化为胸腺嘧啶吡咯烷PNA单体的四种立体异构体，以及（2R,4S）-腺嘌呤、-鸟嘌呤和-胞嘧啶单体的合成，并将其引入到形成双链的PNA寡聚体中。对互补DNA/RNA序列在平行或反平行方向下的杂交研究得到的有趣结果揭示了立体化学依赖的DNA与RNA的区分以及平行/反平行方向的选择性。
• Halogenated substituted mercaptoacylamino acids
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04241076A1

  公开（公告）日：1980-12-23

  New halogen substituted mercaptoacylamino acids which have the general formula ##STR1## and basic salts thereof are useful as hypotensive agents.

  新的卤代硫醇酰胺氨基酸，其一般式为##STR1##及其碱性盐作为降压剂是有用的。
• Studies on Hydroxyproline
  作者：Arthur A. Patchett、Bernhard Witkop

  DOI：10.1021/ja01558a050

  日期：1957.1
• KRAPCHO, JOHN;TURK, CHESTER;CUSHMAN, DAVID W.;POWELL, JAMES R.;DEFORREST,+, J. MED. CHEM., 31,(1988) N 6, C. 1148-1160
  作者：KRAPCHO, JOHN、TURK, CHESTER、CUSHMAN, DAVID W.、POWELL, JAMES R.、DEFORREST,+

  DOI：——

  日期：——
• US4501901A
  申请人：——

  公开号：US4501901A

  公开（公告）日：1985-02-26