Nα-(4-methoxybenzenesulfonyl)-L-phenylalanine | 51866-90-1

• 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: Nα-(4-methoxybenzenesulfonyl)-L-phenylalanine
• 英文别名: N-(4-methoxyphenylsulfonyl)-DL-phenylalanine；(2S)-2-[(4-methoxyphenyl)sulfonylamino]-3-phenylpropanoic acid
• CAS: 51866-90-1
• 化学式: C₁₆H₁₇NO₅S
• mdl: MFCD09749756
• 分子量: 335.381
• InChiKey: DBKQRNHRAQHJGB-HNNXBMFYSA-N

物化性质

• 沸点：
  539.3±60.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  Nα-(4-methoxybenzenesulfonyl)-L-phenylalanine 在 lithium aluminium tetrahydride 、 sodium 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 氨 为溶剂， 反应 24.75h， 生成 (2S)-3-苯基-1,2-丙烷二胺
  参考文献：
  名称：

  Deprotection of Sulfonyl Aziridines

  摘要：

  The deprotection of the chiral N-sulfonyl aziridines 1-3 has been studied under different desulfonylation conditions. Two methods for the efficient deprotection of 2-benzyl-, 2-phenyl-, and 2-carboxyl-N-sulfonylaziridines were found. The desulfonylation with lithium and a catalytic amount of di-tert-butyl biphenyl in THF at -78 degrees C led to the corresponding NH aziridines with yields up to 85%. Alternatively, the desulfonylation could be carried out with magnesium in methanol under ultrasonic conditions. The latter proved to be avery mild method and afforded the desulfonylated aziridines with yields up to 75%, even when the 2-phenyl substituted aziridine 2 was the studied substrate. Furthermore, in all the cases studied, no racemization was observed in the chiral center of the aziridines.

  DOI：

  10.1021/jo9815296
• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 在 甲醇 、 水 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 Nα-(4-methoxybenzenesulfonyl)-L-phenylalanine
  参考文献：
  名称：

  Discovery of a novel GRPR antagonist for protection against cisplatin-induced acute kidney injury

  摘要：

  DOI：

  10.1016/j.bioorg.2022.105794

文献信息

• HIV protease inhibitors based on amino acid derivatives
  申请人：——

  公开号：US20020151546A1

  公开（公告）日：2002-10-17

  A compound selected from the group consisting of a compound of formula I 1 a compound of formula II 2 and when the compound of formula I and II comprises an amino group pharmaceutically acceptable ammonium salts thereof, wherein R 1 , R 2 , Cx, n, R 3 , R 4 , R 5 , Y are as defined in the specification.

  从以下组中选择的化合物，其中化合物I的化合物，化合物II的化合物，以及当化合物I和II的化合物包括其氨基团的药用可接受铵盐，其中R1、R2、Cx、n、R3、R4、R5、Y的定义如规范中所述。
• [EN] PROCESSES FOR THE PREPARATION OF SUBSTITUTED TETRAHYDRO BETA-CARBOLINES<br/>[FR] PROCÉDÉS DE PRÉPARATION DE TÉTRAHYDRO BÊTA-CARBOLINES SUBSTITUÉES
  申请人：PTC THERAPEUTICS INC

  公开号：WO2010138644A1

  公开（公告）日：2010-12-02

  Provided herein are improved processes for the synthesis of substituted tetrahydro beta-carboline derivatives. In particular, provided herein are improved processes useful for the preparation of (S)-4-chlorophenyl 6-chloro- 1 -(4-methoxyphenyl)-3,4-dihydro- 1 H-pyrido [3,4-b]indole-2(9H)-carboxylate. Formula (I)

  本文提供了改进的合成取代四氢β-咔啉衍生物的过程。特别是，本文提供了用于制备(S)-4-氯苯基6-氯-1-(4-甲氧基苯基)-3,4-二氢-1H-吡啶[3,4-b]吲哚-2(9H)-羧酸酯的改进过程。公式(I)
• Preparation of hydroxamic acids from esters in solution and on the solid phase
  申请人：Ho Yung Chih

  公开号：US20060009658A1

  公开（公告）日：2006-01-12

  The present invention provides a novel method for the formation of hydroxamic acids comprising reacting under suitable conditions an ester with hydroxylamine in the presence of cyanide anion.

  本发明提供了一种新颖的羟肟酸形成方法，包括在适当条件下在氰离子存在下将酯与羟胺反应。
• PROCESSES FOR THE PREPARATION OF SUBSTITUTED TETRAHYDRO BETA-CARBOLINES
  申请人：Hwang Peter Seongwoo

  公开号：US20120136154A1

  公开（公告）日：2012-05-31

  Provided herein are improved processes for the synthesis of substituted tetrahydro beta-carboline derivatives. In particular, provided herein are improved processes useful for the preparation of (S)-4-chlorophenyl 6-chloro-1-(4-methoxyphenyl)-3,4-dihydro-1H-pyrido[3,4- b ]indole-2(9H)-carboxylate. Formula (I)

  本文提供了改进的过程，用于合成取代的四氢β-咔啉衍生物。具体而言，本文提供了改进的过程，用于制备(S)-4-氯苯基6-氯-1-(4-甲氧苯基)-3,4-二氢-1H-吡啶[3,4-b]吲哚-2(9H)-羧酸酯。化学式(I)
• Synthesis, anti-HIV and cytotoxicity evaluation of chiral 2,5-disubstituted 1,3,4-thiadiazole derivatives bearing the sulfonamide scaffold
  作者：Anum Israr、Shahid Hameed、Najim A. Al-Masoudi

  DOI：10.1515/znb-2023-0078

  日期：2024.2.26

  In the present study, chiral 2-(4-substiuted phenyl)amino-5-[1-(4-substituted benzenesulphonamido)alkyl]-1,3,4-thiazdiazoles 5a–x were synthesized from enantiopure l-amino acids in a multistep sequence. The starting acids were reacted with arylsulphonyl chlorides to produce N-arylsulfonyl amino acids 1a–h, followed by esterification to obtain the corresponding esters 2a–h. Treatment of esters with hydrazine hydrate afforded the corresponding hydrazides 3a–h. The coupling of hydrazides with aryl isothiocyanates followed by cyclization gave the target thiadiazoles 5a–x in good yields. The new synthesized compounds were assayed against HIV-1 and HIV-2 in MT-4 cells using MTT assay. Compounds 5s, 5v and 5w showed IC₅₀ values of > 1.58, >1.98 and > 2.04 μm with SI > 1, respectively, indicating that these compounds were cytotoxic at concentrations values of 1.58, 1.98 and 2.04 μm, respectively.

  摘要 本研究以对映体纯的 l-氨基酸为原料，通过多步骤合成了手性 2-(4-取代苯基)氨基-5-[1-(4-取代苯磺酰胺基)烷基]-1,3,4-噻二唑 5a-x。起始酸与芳基磺酰氯反应生成 N-芳基磺酰基氨基酸 1a-h，然后进行酯化反应得到相应的酯 2a-h。用肼水合物处理酯类可得到相应的肼 3a-h。酰肼与芳基异硫氰酸酯偶联后环化，得到目标噻二唑 5a-x，收率很高。利用 MTT 法检测了新合成化合物在 MT-4 细胞中对 HIV-1 和 HIV-2 的作用。化合物 5s、5v 和 5w 的 IC50 值分别为 1.58、1.98 和 2.04 μm（SI 值为 1），表明这些化合物在 1.58、1.98 和 2.04 μm 浓度下具有细胞毒性。