benzyl 2R-trifluoromethanesulfonyloxy-4-methylvalerate | 130317-28-1

• 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: benzyl 2R-trifluoromethanesulfonyloxy-4-methylvalerate
• 英文别名: benzyl 2-(R)-trifluoromethanesulfonyloxy-4-methylpentanoate；benzyl (2R)-4-methyl-2-(trifluoromethylsulfonyloxy)pentanoate
• CAS: 130317-28-1
• 化学式: C₁₄H₁₇F₃O₅S
• 分子量: 354.347
• InChiKey: RMGDNLNVSBPAGS-GFCCVEGCSA-N

物化性质

• 沸点：
  373.3±42.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 2R-trifluoromethanesulfonyloxy-4-methylvalerate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 2-(tert-butoxycarbonyl)-(3R)-3-isobutylsuccinic acid
  参考文献：
  名称：

  Synthesis of an Inhibitor-Tethered Resin for Detection of Active Matrix Metalloproteinases Involved in Disease

  摘要：

  Matrix metalloproteinases ( MMPs), of which 26 members are known in humans, are implicated in a number of diseases. Their activity is strictly controlled, but when the biological control over the activity is lost, disease processes set in. In an attempt to delineate what MMP activity has gone awry in what diseases, including metastatic cancers that are of special interest to our laboratories, we conceived and synthesized two chromatographic resins incorporated with a multifunctional broad- spectrum inhibitor for MMPs. The broad-spectrum inhibitor contains three sterogentic centers and was synthesized in 13 steps. Two structural variants of the inhibitors were linked to the polymer support via disulfide moieties. These resins are intended for use in cellular systems to selectively fish out from a complex mixture of all cellular proteins the active MMP forms important for the specific disease for identification.

  DOI：

  10.1021/jo060058h
• 作为产物：
  描述：

  D-亮氨酸 在 2,6-二甲基吡啶 、 硫酸 、 水 、 caesium carbonate 、 sodium nitrite 作用下， 生成 benzyl 2R-trifluoromethanesulfonyloxy-4-methylvalerate
  参考文献：
  名称：

  酰肼γ-转模拟物的研究进展

  摘要：

  蒙特卡洛（Monte Carlo）的计算显示了一系列称为二甲双胍的代谢产物的经典γ转变。这导致了从亮氨酸开始的差向异构体七元环γ-转类似物的合成。还进行了NMR温度系数研究。

  DOI：

  10.1016/s0040-4039(97)01664-x

文献信息

• Prodrugs of E‐selectin Antagonists with Enhanced Pharmacokinetic Properties
  作者：Philipp Dätwyler、Xiaohua Jiang、Beatrice Wagner、Norbert Varga、Tobias Mühlethaler、Katja Hostettler、Said Rabbani、Oliver Schwardt、Beat Ernst

  DOI：10.1002/cmdc.202100634

  日期：2022.1.5

  addition of lipophilic ester moieties to overcome insufficient lipophilicity of selectin antagonists was found to improve passive permeation into enterocytes; however, at the same time it supported efflux back to the small intestines as well as oxidation into non-hydrolysable metabolites. Our examples demonstrate that prodrug modifications of carbohydrates can result in opposing effects and must therefore

  了解整个故事：发现添加亲脂性酯部分以克服选择素拮抗剂的亲脂性不足，从而改善对肠细胞的被动渗透；然而，同时它支持外排回到小肠以及氧化成不可水解的代谢物。我们的例子表明，碳水化合物的前体药物修饰会导致相反的效果，因此必须对其进行整体研究。
• [EN] HALOALKYL FUCOSE-CONTAINING SELECTIN ANTAGONISTS<br/>[FR] ANTAGONISTES DE LA SÉLECTINE CONTENANT DE L'HALOALKYL-FUCOSE
  申请人：GLYCOMIMETICS INC

  公开号：WO2017205269A1

  公开（公告）日：2017-11-30

  Compounds of Formula (I), compositions, and methods for treatment and/or prevention of at least one disease, disorder, and/or condition by inhibiting binding of an E-selectin to an E-selectin ligand are disclosed. For example, haloalkyl fucose-containing E-selectin antagonists and compositions comprising at least one such agent are described.

  公式（I）的化合物、组合物以及通过抑制E-选择素与E-选择素配体结合来治疗和/或预防至少一种疾病、紊乱和/或状况的方法被揭示。例如，描述了含有卤代糖基的E-选择素拮抗剂和包含至少一种此类药剂的组合物。
• The development of hydrazide γ-turn mimetics
  作者：Mark D. Ferguson、Joseph P. Meara、Hiroshi Nakanishi、Min S. Lee、Michael Kahn

  DOI：10.1016/s0040-4039(97)01664-x

  日期：1997.10

  Monte Carlo calculations show a classical γ-turn in a family of metabolites known as the malformins. This led to the synthesis of epimeric seven-membered ring γ-turn mimetics starting from leucine. NMR temperature coefficient studies were also performed.

  蒙特卡洛（Monte Carlo）的计算显示了一系列称为二甲双胍的代谢产物的经典γ转变。这导致了从亮氨酸开始的差向异构体七元环γ-转类似物的合成。还进行了NMR温度系数研究。
• ACE-2 modulating compounds and methods of use thereof
  申请人：——

  公开号：US20040082496A1

  公开（公告）日：2004-04-29

  ACE-2 modulating compounds for the treatment of body weight disorders are disclosed. Methods of using the compounds and pharmaceutical compositions containing the compounds are also claimed.

  抗ACE-2调节化合物用于治疗体重失调的方法已被披露。还声称了使用这些化合物的方法和含有这些化合物的药物组合物。
• Aminophosphonic acid derivative
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0623625A1

  公开（公告）日：1994-11-09

  There are provided novel aminophosphonic acid derivatives of the general formula [I]: wherein n is an integer of 2 or 3; R¹ is a phenyl, naphthyl, indolyl, benzothienyl, benzofuryl or benzoxazolyl group which may have 1 to 3 substituents selected from the group consisting of hydroxyl and lower alkyloxy groups, or a hydrogen atom; R² is a lower alkyl group, a benzyl group, a 4-hydroxybenzyl group, a 3-indolylmethyl group or a β-phenethyl group; and A is an optional residue of an amino acid selected from the group consisting of tryptophane, tyrosine, phenylalanine, homophenylalanine, naphthylalanine or Nω-nitroarginine, and their pharmaceutically acceptable salts. The compounds according to the present invention and their pharmaceutically acceptable salts exhibit an inhibitory activity against endothelin-converting enzyme, and are expected to be useful as a drug treating various diseases with which endothelin is concerned.

  提供了一种新型的氨基膦酸衍生物，其一般式如下[I]：其中n是2或3的整数；R¹是苯基，萘基，吲哚基，苯并噻吩基，苯并呋喃基或苯并噁唑基，其可具有1至3个取自氢氧基和低烷氧基的取代基，或是氢原子；R²是低烷基，苄基，4-羟基苄基，3-吲哚甲基基或β-苯乙基；A是选自色氨酸，酪氨酸，苯丙氨酸，同型苯丙氨酸，萘氨酸或Nω-硝基精氨酸的氨基酸残基，以及它们的药学上可接受的盐。根据本发明的化合物及其药学上可接受的盐表现出对内皮素转化酶的抑制活性，预计可用于治疗与内皮素相关的各种疾病的药物。