(3R,5S)-5-(methoxycarbonyl)-1-acetylpyrrolidin-3-yl 4-methylbenzenesulfonate | 57750-51-3

• 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: (3R,5S)-5-(methoxycarbonyl)-1-acetylpyrrolidin-3-yl 4-methylbenzenesulfonate
• 英文别名: Methyl N-acetyl-4(R)-(p-toluenesulfonyloxy)pyrrolidine-2(S)-carboxylate；methyl (2S,4R)-1-acetyl-4-(tosyloxy)pyrrolidine-2-carboxylate；Methyl N-Acetyl-trans-4-(tosyloxy)-L-prolinate；trans-1-acetyl-4-(toluene-4-sulfonyloxy)-L-proline methyl ester；trans-1-Acetyl-4-(toluol-4-sulfonyloxy)-L-prolin-methylester；methyl (2S,4R)-1-acetyl-4-(4-methylphenyl)sulfonyloxypyrrolidine-2-carboxylate
• CAS: 57750-51-3
• 化学式: C₁₅H₁₉NO₆S
• 分子量: 341.385
• InChiKey: KCONJLWEYUCWTH-OCCSQVGLSA-N

物化性质

• 沸点：
  515.8±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,5S)-5-(methoxycarbonyl)-1-acetylpyrrolidin-3-yl 4-methylbenzenesulfonate 在 sodium hydroxide 作用下， 生成 cis-1-acetyl-4-hydroxy-DL-proline
  参考文献：
  名称：

  Neuberger, Journal of the Chemical Society, 1945, p. 431

  摘要：

  DOI：
• 作为产物：
  描述：

  N-乙酰-L-4-羟基脯氨酸 在 1,4-二氧六环 、 吡啶 、 乙醚 作用下， 生成 (3R,5S)-5-(methoxycarbonyl)-1-acetylpyrrolidin-3-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Neuberger, Journal of the Chemical Society, 1945, p. 431

  摘要：

  DOI：

文献信息

• 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/
  作者：M. Umashankara、I. Ramesh Babu、Krishna N. Ganesh

  DOI：10.1039/b308581c

  日期：——

  4R/S-Aminoprolines when present in the X-position of collagen peptide [pro(X)-pro(Y)-Gly]n exhibit pH- and stereochemistry-dependent effects on triplex stability.

  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。
• Design, synthesis and preliminary evaluation of novel pyrrolidine derivatives as matrix metalloproteinase inhibitors
  作者：Xian-Chao Cheng、Qiang Wang、Hao Fang、Wei Tang、Wen-Fang Xu

  DOI：10.1016/j.ejmech.2007.12.020

  日期：2008.10

  of novel pyrrolidine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and aminopeptidase N (AP-N). The results showed that these pyrrolidine derivatives exhibited highly selective inhibition against MMP-2 as compared with AP-N. The hydroxamates 8a-c were equally or more potent MMP-2 inhibitors than the positive control LY52. The

  设计，合成和测定了一系列新颖的吡咯烷衍生物对基质金属蛋白酶2（MMP-2）和氨基肽酶N（AP-N）的抑制活性。结果表明，与AP-N相比，这些吡咯烷衍生物表现出对MMP-2的高度选择性抑制。异羟肟酸酯8a-c是与阳性对照LY52同等或更有效的MMP-2抑制剂。提出了最有效的化合物8a与MMP-2的结合方式。构效关系也作了简要讨论。
• Sulfinic acids and related compounds. 13. Unsymmetrical disulfides based on methyl 4-mercaptobutanesulfinate and 4(S)- or 4(R)-mercaptoprolines
  作者：Venkatachalam Eswarakrishnan、Lamar Field

  DOI：10.1021/jo00334a015

  日期：1981.10
• Identification of novel TACE inhibitors compatible with topical application
  作者：Gilles Ouvry、Yaël Berton、Yushma Bhurruth-Alcor、Laetitia Bonnary、Claire Bouix-Peter、Karine Bouquet、Marilyne Bourotte、Sandrine Chambon、Catherine Comino、Benoît Deprez、Denis Duvert、Gwenaëlle Duvert、Feriel Hacini-Rachinel、Craig S. Harris、Anne-Pascale Luzy、Arnaud Mathieu、Corinne Millois、Jonathan Pascau、Artur Pinto、Gaëlle Polge、Arnaud Reitz、Kevin Reversé、Carine Rosignoli、Nathalie Taquet、Laurent F. Hennequin

  DOI：10.1016/j.bmcl.2017.02.035

  日期：2017.4

  Targeting the Tumor Necrosis Factor cc signalling with antibodies has led to a revolution in the treatment of psoriasis. Locally inhibiting Tumor Necrosis Factor alpha. Converting Enzyme (TACE or ADAM17) could potentially mimic those effects and help treat mild to moderate psoriasis, without the reported side effect of systemic TACE inhibitors. Efforts to identify new TACE inhibitors are presented here. Enzymatic SAR as well as ADME and physico-chemistry data are presented. This study culminated in the identification of potent enzymatic inhibitors. Suboptimal cellular activity of this series is discussed in the context of previously published results. (C) 2017 Elsevier Ltd. All rights reserved.
• Studies on Hydroxyproline
  作者：Arthur A. Patchett、Bernhard Witkop

  DOI：10.1021/ja01558a050

  日期：1957.1

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