N-[(2S)-1-hydrazinyl-1-oxo-3-phenylpropan-2-yl]-4-methylbenzenesulfonamide | 1023645-02-4

• 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: N-[(2S)-1-hydrazinyl-1-oxo-3-phenylpropan-2-yl]-4-methylbenzenesulfonamide
• CAS: 1023645-02-4
• 化学式: C₁₆H₁₉N₃O₃S
• 分子量: 333.411
• InChiKey: XADHSRFALGIDAW-HNNXBMFYSA-N

物化性质

• 密度：
  1.282±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(2S)-1-hydrazinyl-1-oxo-3-phenylpropan-2-yl]-4-methylbenzenesulfonamide 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 2-(4-bromophenyl)amino-5-(1-(4-methylbenzenesulphonamido)-2-phenylethyl)-1,3,4-thiadiazole
  参考文献：
  名称：

  Synthesis, anti-HIV and cytotoxicity evaluation of chiral 2,5-disubstituted 1,3,4-thiadiazole derivatives bearing the sulfonamide scaffold

  摘要：

  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。

  DOI：

  10.1515/znb-2023-0078
• 作为产物：
  描述：

  N-(p-toluenesulfonyl)-L-phenylalanine methyl ester 在 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 生成 N-[(2S)-1-hydrazinyl-1-oxo-3-phenylpropan-2-yl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis and antiviral activities of novel acylhydrazone derivatives targeting HIV-1 capsid protein

  摘要：

  HIV-1 capsid protein (CA) plays important roles in the viral replication cycle. A number of acylhydrazone derivatives that act as inhibitors of HIV-1 CA assembly, were designed and synthesized. The synthesized compounds were tested for their antiviral activities and cytotoxicities using CEM cells. Some derivatives also were assayed for their ability to inhibit HIV-1 CA assembly in vitro. Among them, compounds 14f and 14i display the most promising potency with EC50 values of 0.21 and 0.17 mu M, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.116

文献信息

• Synthesis and antiviral activities of novel acylhydrazone derivatives targeting HIV-1 capsid protein
  作者：Baohe Tian、Meizi He、Shixing Tang、Indira Hewlett、Zhiwu Tan、Jiebo Li、Yinxue Jin、Ming Yang

  DOI：10.1016/j.bmcl.2009.02.116

  日期：2009.4

  HIV-1 capsid protein (CA) plays important roles in the viral replication cycle. A number of acylhydrazone derivatives that act as inhibitors of HIV-1 CA assembly, were designed and synthesized. The synthesized compounds were tested for their antiviral activities and cytotoxicities using CEM cells. Some derivatives also were assayed for their ability to inhibit HIV-1 CA assembly in vitro. Among them, compounds 14f and 14i display the most promising potency with EC50 values of 0.21 and 0.17 mu M, respectively. (C) 2009 Elsevier Ltd. All rights reserved.
• 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。