(S)-2-Acetylsulfanylmethyl-pyrrolidine-1-carboxylic acid benzyl ester | 101250-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-Acetylsulfanylmethyl-pyrrolidine-1-carboxylic acid benzyl ester
• 英文别名: benzyl (2S)-2-(acetylsulfanylmethyl)pyrrolidine-1-carboxylate
• CAS: 101250-72-0
• 化学式: C₁₅H₁₉NO₃S
• 分子量: 293.387
• InChiKey: NHHXOBGHKFMZBL-AWEZNQCLSA-N

物化性质

• 沸点：
  425.9±28.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-Acetylsulfanylmethyl-pyrrolidine-1-carboxylic acid benzyl ester 在 一水合肼 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 (S)-phenylmethyl 2-(mercaptomethyl)-1-pyrrolidinecarboxylate
  参考文献：
  名称：

  Modified di- and tripeptides of the C-terminal portion of oxytocin and vasopressin as possible cognition activation agents

  摘要：

  A number of peptides and modified peptides were synthesized and studied for their ability to reverse electroconvulsive shock-induced amnesia in rodents. A few of these peptides were selected for secondary evaluation in tests of short-term memory in rats and aged rhesus monkeys. A number of the peptides and modified peptides were active in the amnesia reversal test. In selected secondary tests, however, the chosen compounds failed to show significant activity in enhancing memory. New methods for preparing methyleneamino and methyleneoxy isosteres of peptides are reported. Other modified peptides also included methylenethio, methylenesulfonyl, and ethylene isosteres in place of the normal peptide amide bond.

  DOI：

  10.1021/jm00156a012
• 作为产物：
  描述：

  L-脯氨醇 在 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-2-Acetylsulfanylmethyl-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  高效而简便的合成 ñ-Cbz-β-氨基链烷磺酰胺

  摘要：

  描述了一种合成N -Cbz-β-氨基链烷磺酰胺的有效方法。N -Cbz-β-氨基链烷磺酰胺很容易以高收率由多种氨基醇（包括旋光性氨基醇）制备，方法是用氯甲酸苄酯进行N -Cbz保护，用硫代乙酸进行Mitsunobu酯化反应，N-氯代琥珀酰亚胺氧化和氨解处理。

  DOI：

  10.1007/s11426-012-4607-9

文献信息

• Targeted Covalent Inhibition of Prolyl Oligopeptidase (POP): Discovery of Sulfonylfluoride Peptidomimetics
  作者：Salvador Guardiola、Roger Prades、Laura Mendieta、Arwin J. Brouwer、Jelle Streefkerk、Laura Nevola、Teresa Tarragó、Rob M.J. Liskamp、Ernest Giralt

  DOI：10.1016/j.chembiol.2018.04.013

  日期：2018.8

  Prolyl oligopeptidase (POP), a serine protease highly expressed in the brain, has recently emerged as an enticing therapeutic target for the treatment of cognitive and neurodegenerative disorders. However, most reported inhibitors suffer from short duration of action, poor protease selectivity, and low blood-brain barrier (BBB) permeability, which altogether limit their potential as drugs. Here, we

  脯氨酰寡肽酶（POP）是一种在大脑中高度表达的丝氨酸蛋白酶，最近已成为治疗认知和神经退行性疾病的诱人治疗靶标。然而，大多数报道的抑制剂具有作用时间短，蛋白酶选择性差和血脑屏障（BBB）渗透性低的缺点，这完全限制了它们作为药物的潜力。在这里，我们描述了第一个不可逆的，选择性的和脑可渗透的POP抑制剂的基于结构的设计。在低纳摩尔浓度下，这些共价拟肽在体外和在人细胞中都能快速，特异性和持续地灭活POP。更重要的是，它们对两种家族相关蛋白酶（DPPIV和FAP）的选择性> 1,000倍，并且显示出高的BBB渗透性，如脂膜和MDCK细胞中所示。
• Efficient synthesis of protected sulfonopeptides from N-protected 2-aminoalkyl xanthates and thioacetates
  作者：Saeed Kakaei、Jiaxi Xu

  DOI：10.1016/j.tet.2013.08.028

  日期：2013.10

  An efficient and convenient method was developed for the synthesis of protected sulfonopeptides via N-chlorosuccimide (NCS)/HCI oxidative chlorination of N-protected 2-aminoallcyl xanthates or thioacetates to the corresponding sulfonyl chlorides followed by aminolysis with amino esters. In the current method, sulfonopeptides containing 1- and 2-substituted taurines were prepared in satisfactory to good yields. It is a useful and efficient strategy for the synthesis of protected sulfonopeptides with functionalized side-chains. (C) 2013 Elsevier Ltd. All rights reserved.
• N-acylamino acid derivatives and their use
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0309766B1

  公开（公告）日：1998-04-15
• US5122523A
  申请人：——

  公开号：US5122523A

  公开（公告）日：1992-06-16
• US5240924A
  申请人：——

  公开号：US5240924A

  公开（公告）日：1993-08-31