2-methyl-N-[(2-nitrophenyl)sulfonyl]alanine | 324016-48-0

• 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: 2-methyl-N-[(2-nitrophenyl)sulfonyl]alanine
• 英文别名: 2-methyl-2-[(2-nitrophenyl)sulfonylamino]propanoic acid
• CAS: 324016-48-0
• 化学式: C₁₀H₁₂N₂O₆S
• mdl: MFCD13325976
• 分子量: 288.281
• InChiKey: SZWKJUDEFRTWLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-methyl-N-[(2-nitrophenyl)sulfonyl]alanine 在 1-氯-N,N,2-三甲基丙烯胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Incorporation of CF₃–Pseudoprolines into Peptides: A Methodological Study

  摘要：

  The peptide coupling reactions allowing the incorporation of trifluoromethyl substituted oxazolidine-type pseudoprolines (CF3-Psi Pro) into peptide chains have been studied. While standard protocols can be used for the peptide coupling reaction at the C-terminal position of the CF3-Psi Pro, acid chloride activation has to be used for the peptide coupling reaction at the N-terminal position to overcome the decrease of nucleophilicity of the CF3-Psi Pro. We demonstrate that the N-amidification of a diastereomeric mixture of CF3-Psi Pro using Fmoc-protected amino acid chloride without base gave the corresponding dipeptides as a single diastereomer (6 examples). The ratio of the cis and trans amide bond conformers was determined by NMR study, highlighting the role of the Xaa side chains in the control of the peptide backbone conformation. Finally a tripeptide bearing a central CF3-Psi Pro has been successfully synthesized.

  DOI：

  10.1021/jo401494q
• 作为产物：
  描述：

  methyl 2-methyl-2-(2-nitrophenylsulfonamido)propanoate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以2.46 g的产率得到2-methyl-N-[(2-nitrophenyl)sulfonyl]alanine
  参考文献：
  名称：

  PEPTIDE SYNTHESIS METHOD FOR SUPPRESSING DEFECT CAUSED BY DIKETOPIPERAZINE FORMATION

  摘要：

  Solid-phase synthesis of a peptide has a problem that a desired elongation reaction is prevented from proceeding by diketopiperazine and a 6-membered diamine skeleton compound formed when a protective group at the N-terminal is removed. The present inventors have found that when in production of a peptide by a solid-phase method, a peptide in which an amino group at the N-terminal is protected with a protective group having an Fmoc skeleton is treated in a specific solvent with a base having a pKa of 23 or more in acetonitrile as a conjugate acid, and a peptide chain is then elongated, it is possible to solve the problem described above.

  公开号：

  US20230391818A1

文献信息

• A COMPOUND FOR INHIBITING 11B-HYDROXY STEROID DEHYDROGENASE 1, AND A PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
  申请人：Lee Inhee

  公开号：US20140206875A1

  公开（公告）日：2014-07-24

  Disclosed are a novel compound or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition including the same for inhibiting human 11-β-hydroxy steroid dehydrogenase type 1 (11β-HSD1). The disclosed compound and the pharmaceutical composition including the same for inhibiting human 11-β-hydroxy steroid dehydrogenase type 1 (11β-HSD1) are excellent in activity and solubility, and is more efficient in formulation and transfer.

  本文披露了一种新型化合物或其药用可接受的盐，以及包括该化合物的药物组合物，用于抑制人类11-β-羟基类固醇脱氢酶1型（11β-HSD1）。所披露的化合物和包括该化合物的药物组合物用于抑制人类11-β-羟基类固醇脱氢酶1型（11β-HSD1）在活性和溶解性方面表现出色，并且在配方和转移方面更为高效。
• Two<i>N</i>-<i>ortho</i>-nitrobenzenesulfonyl α,α-disubstituted amino acid adducts
  作者：Lars G. J. Hammarström、Tao Zhang、José Giraldés、Mark L. McLaughlin、Damon R. Billodeaux、Frank R. Fronczek

  DOI：10.1107/s0108270100012464

  日期：2000.12.15

  The carboxy group of 2-methyl-N-[(2-nitrophenyl)sulfonyl]alanine, C10H12N2O6S, forms centrosymmetric hydrogen-bonded dimers with an O . . .O distance of 2.629 (2) Angstrom and an intramolecular N-H . . .O(nitro) hydrogen bond N . . .O distance of 2.823 (2) Angstrom. 1-[(2-Nitrophenyl)sulfonylamino]cyclohexanecarboxylic acid, C13H16N2O6S, has Z' = 2 and forms similar interactions.
• US9073830B2
  申请人：——

  公开号：US9073830B2

  公开（公告）日：2015-07-07
• [EN] A COMPOUND FOR INHIBITING 11ß-HYDROXY STEROID DEHYDROGENASE 1, AND A PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] COMPOSÉ D'INHIBITION DE LA 11?-HYDROXYSTÉROÏDE DÉSHYDROGÉNASE DE TYPE 1, ET COMPOSITION PHARMACEUTIQUE LE COMPRENANT
  申请人：HYUNDAI PHARM CO LTD

  公开号：WO2013019091A2

  公开（公告）日：2013-02-07

  Disclosed are a novel compound or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition including the same for inhibiting human 11-β-hydroxy steroid dehydrogenase type 1 (11β-HSD1).　The disclosed compound and the pharmaceutical composition including the same for inhibiting human 11-β-hydroxy steroid dehydrogenase type 1 (11β-HSD1) are excellent in activity and solubility, and is more efficient in formulation and transfer.
• [EN] PEPTIDE SYNTHESIS METHOD FOR SUPPRESSING DEFECT CAUSED BY DIKETOPIPERAZINE FORMATION<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE PEPTIDE POUR SUPPRIMER UN DÉFAUT PROVOQUÉ PAR LA FORMATION DE DICÉTOPIPÉRAZINE<br/>[JA] ジケトピペラジン形成による欠損を抑制するペプチド合成方法
  申请人：[en]CHUGAI SEIYAKU KABUSHIKI KAISHA;[ja]中外製薬株式会社

  公开号：WO2022097540A1

  公开（公告）日：2022-05-12

  ペプチドの固相合成においては、Ｎ末端の保護基を除去する際に形成されるジケトピペラジン、および６員環状アミジン骨格構造体に起因して、所望の伸長反応が進行しないという課題がある。本発明者らは、固相法によるペプチドの製造において、特定の溶媒中、共役酸のアセトニトリル中でのｐＫａが２３以上である塩基を用いてＦｍｏｃ骨格を有する保護基にてＮ末端のアミノ基が保護されたペプチドを処理し、次いで、ペプチド鎖の伸長を行うことで、上記の課題を解決できることを見出した。