methyl N-(phenylsulfonyl)-DL-serinate | 184592-41-4

• 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: methyl N-(phenylsulfonyl)-DL-serinate
• 英文别名: 2-Benzenesulfonylamino-3-hydroxy-propionic acid methyl ester；methyl 2-(benzenesulfonamido)-3-hydroxypropanoate
• CAS: 184592-41-4
• 化学式: C₁₀H₁₃NO₅S
• mdl: MFCD12643161
• 分子量: 259.283
• InChiKey: FZFLJJRZBOUHCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl N-(phenylsulfonyl)-DL-serinate 在 咪唑 、 4-二甲氨基吡啶 、 锂硼氢 、 potassium tert-butylate 、 四丁基氟化铵 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 81.0h， 生成 3,5-Bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoic acid 2-benzenesulfonylamino-3-(4-benzyloxy-phenoxy)-propyl ester
  参考文献：
  名称：

  Synthesis and Protein Kinase C Inhibitory Activities of Acyclic Balanol Analogs That Are Highly Selective for Protein Kinase C over Protein Kinase A

  摘要：

  A series of balanol analogs in which the perhydroazepine ring and the p-hydroxybenzamide moiety were combined into an acyclic linked unit have been prepared and evaluated for their inhibitory properties against the serine/threonine kinase PKC. Several low-micromolar to low-nanomolar inhibitors of the alpha, beta(I), beta(II), gamma, delta, epsilon, and eta PKC: isozymes were prepared. In general, these acyclic balanol analogs were found to be highly selective for PKC over the serine/threonine kinase PKA. The type and number of atoms linking the benzophenone ester to the p-hydroxyphenyl group necessary for optimal PKC inhibition were investigated. The most potent compounds contained a three-carbon linker in which the carboxamide moiety of balanol had been replaced by a methylene group. The effect of placing substituents on the three-carbon chain was also investigated. The preferred compounds contained either a 2-benzenesulfonamido (6b) or a 1-methyl (21b) substituent. The preferred compounds 6b and 21b were tested against a panel of serine/threonine kinases and found to be highly selective for PKC. The more active enantiomer of 6b, (S)-12b, was 3-10-fold more active than the R-enantiomer against the PKC isozymes. The effect of making the analogs more rigid by making the three-carbon chain part of a five-membered ring, but with retention of the methylene replacement for the carboxamide moiety, led to potent PKC inhibitors including anti-substituted pyrrolidine analog 35b and the most potent PKC inhibitor in the series, anti-substituted cyclopentane analog 29b. The anti cyclopentane analog 29b was a low-micromolar inhibitor of the PMA-induced superoxide burst in neutrophils, and its carboxylic ester was a high-nanomolar inhibitor of neutrophils. Finally esterification of 21b, (S)-12b, and 35b turned these potent PKC inhibitors into low-micromolar inhibitors of neutrophils.

  DOI：

  10.1021/jm960581w
• 作为产物：
  描述：

  DL-丝氨酸甲酯盐酸盐 、 苯磺酰氯 以to give 2-benzenesulfonylamino-3-hydroxy-propionic acid methyl ester的产率得到methyl N-(phenylsulfonyl)-DL-serinate
  参考文献：
  名称：

  IMIDAZOLIDINONE DERIVATIVES

  摘要：

  这项发明涉及公式(I)的新型咪唑啉酮衍生物，其中R1到R11和X如描述和权利要求中所定义，并且其生理上可接受的盐。这些化合物与LXR alpha和LXR beta结合，可用于制备药物组合物。

  公开号：

  US20080242677A1

文献信息

• Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols
  作者：Gabriele Laudadio、Efstathios Barmpoutsis、Christiane Schotten、Lisa Struik、Sebastian Govaerts、Duncan L. Browne、Timothy Noël

  DOI：10.1021/jacs.9b02266

  日期：2019.4.10

  continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts

  磺酰胺是药物和农用化学品中的关键基序，推动了对获取这些官能团的新型有效合成方法的不断开发。在此，我们报告了一种环境友好的电化学方法，该方法可以实现硫醇和胺之间的氧化偶联，这两种容易获得且价格低廉的商品化学品。转化完全由电力驱动，不需要任何牺牲试剂或额外的催化剂，只需5分钟即可完成。氢气在对电极处作为良性副产物形成。由于反应条件温和，该反应显示出广泛的底物范围和官能团兼容性。
• IMIDAZOLIDINONE DERIVATIVES
  申请人：Dehmlow Henrietta

  公开号：US20080242677A1

  公开（公告）日：2008-10-02

  The invention is concerned with novel imidazolidinone derivatives of formula (I): wherein R 1 to R 11 and X are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds bind to LXR alpha and LXR beta and can be used in pharmaceutical compositions.

  这项发明涉及式(I)的新型咪唑烷酮衍生物：其中R1到R11和X如描述和索取中定义的那样，以及其生理学上可接受的盐。这些化合物与LXRα和LXRβ结合，可用于制备药物组合物。
• Imidazolidinone derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US07625902B2

  公开（公告）日：2009-12-01

  The invention is concerned with novel imidazolidinone derivatives of formula (I): wherein R1 to R11 and X are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds bind to LXR alpha and LXR beta and can be used in pharmaceutical compositions.

  本发明涉及式(I)的新型咪唑啉酮衍生物，其中R1至R11和X在说明书和权利要求书中定义，以及其生理上可接受的盐。这些化合物与LXR alpha和LXR beta结合，可用于制备药物组合物。
• Metal oxide in aqueous organic solution promoted chemoselective N-sulfonylation of hydrophilic amino alcohols
  作者：Hak Hee Kang、Ho Sik Rho、Duck Hee Kim、Seong-Geun Oh

  DOI：10.1016/s0040-4039(03)01666-6

  日期：2003.9

  The reaction of hydrophilic amino alcohols with sulfonyl chlorides in the presence of metal oxide (MgO, CuO, Ag2O) in aqueous organic solution cleanly provided alkanolsulfonamide. Advantages of this method were mild, neutral reaction conditions, chemoselectivity and easy isolation of the final product. (C) 2003 Published by Elsevier Ltd.
• US7625902B2
  申请人：——

  公开号：US7625902B2

  公开（公告）日：2009-12-01