(2S)-2-[(2,5-dichlorophenyl)sulfonylamino]pentanedioic acid | 112537-42-5

• 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: (2S)-2-[(2,5-dichlorophenyl)sulfonylamino]pentanedioic acid
• CAS: 112537-42-5
• 化学式: C₁₁H₁₁Cl₂NO₆S
• 分子量: 356.183
• InChiKey: KZXSGGNJMBZYRI-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(2,5-dichlorophenyl)sulfonylamino]pentanedioic acid 在 氯化亚砜 作用下， 生成 (2S)-2-[(2,5-dichlorophenyl)sulfonylamino]pentanedioyl dichloride
  参考文献：
  名称：

  Possible anticancer agents: QSAR analogs of glutamamide: Synthesis and pharmacological activity of 1,5-N,N′-disubstituted-2-(substituted benzenesulphonyl) glutamamides

  摘要：

  Based on our earlier QSAR prediction, a series of designed QSAR analogs of 1,5-N,N'-disubstituted-2-(substituted benzenesulphonyl) glutamamides were synthesized as possible anticancer agents. Inhibitions of tumor cell proliferation of the compounds were tested in tumor cell line IMR-32. Anticancer activities of these compounds were also evaluated on Swiss Albino mice against Ehrlich Ascites Carcinoma (EAC) cells. Tumor weight inhibition and tumor cell inhibition were considered as anticancer activity parameters. QSAR analysis of these compounds was performed on the basis of a set of descriptors like physicochemical, topological, quantum chemical and DRAGON whole molecular descriptors. The study showed that the increase of length of substituent at R-2 position and the increase of dipole moment of the molecule decrease the anticancer activity of these compounds, presence of bromine atom at R-3 position and hydrophilic substitution at R-2 position are advantageous to the activity. Nucleophilic attack at atom number 14 is advantageous and electrophilic attack at atom number 15 is detrimental to anticancer activity. Atom number 2 is important and may be involved in dispersive interactions of the compounds with enzymes. The results offer an opportunity for further tailoring of these analogs for an active member. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.008
• 作为产物：
  描述：

  L-谷氨酸 、 2,5-二氯苄磺酸氯 以90%的产率得到(2S)-2-[(2,5-dichlorophenyl)sulfonylamino]pentanedioic acid
  参考文献：
  名称：

  Possible anticancer agents: QSAR analogs of glutamamide: Synthesis and pharmacological activity of 1,5-N,N′-disubstituted-2-(substituted benzenesulphonyl) glutamamides

  摘要：

  Based on our earlier QSAR prediction, a series of designed QSAR analogs of 1,5-N,N'-disubstituted-2-(substituted benzenesulphonyl) glutamamides were synthesized as possible anticancer agents. Inhibitions of tumor cell proliferation of the compounds were tested in tumor cell line IMR-32. Anticancer activities of these compounds were also evaluated on Swiss Albino mice against Ehrlich Ascites Carcinoma (EAC) cells. Tumor weight inhibition and tumor cell inhibition were considered as anticancer activity parameters. QSAR analysis of these compounds was performed on the basis of a set of descriptors like physicochemical, topological, quantum chemical and DRAGON whole molecular descriptors. The study showed that the increase of length of substituent at R-2 position and the increase of dipole moment of the molecule decrease the anticancer activity of these compounds, presence of bromine atom at R-3 position and hydrophilic substitution at R-2 position are advantageous to the activity. Nucleophilic attack at atom number 14 is advantageous and electrophilic attack at atom number 15 is detrimental to anticancer activity. Atom number 2 is important and may be involved in dispersive interactions of the compounds with enzymes. The results offer an opportunity for further tailoring of these analogs for an active member. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.008

文献信息

• Possible anticancer agents: QSAR analogs of glutamamide: Synthesis and pharmacological activity of 1,5-N,N′-disubstituted-2-(substituted benzenesulphonyl) glutamamides
  作者：Soma Samanta、Sk. Mahasin Alam、Parthasarathi Panda、Tarun Jha

  DOI：10.1016/j.ejmech.2008.03.008

  日期：2009.1

  Based on our earlier QSAR prediction, a series of designed QSAR analogs of 1,5-N,N'-disubstituted-2-(substituted benzenesulphonyl) glutamamides were synthesized as possible anticancer agents. Inhibitions of tumor cell proliferation of the compounds were tested in tumor cell line IMR-32. Anticancer activities of these compounds were also evaluated on Swiss Albino mice against Ehrlich Ascites Carcinoma (EAC) cells. Tumor weight inhibition and tumor cell inhibition were considered as anticancer activity parameters. QSAR analysis of these compounds was performed on the basis of a set of descriptors like physicochemical, topological, quantum chemical and DRAGON whole molecular descriptors. The study showed that the increase of length of substituent at R-2 position and the increase of dipole moment of the molecule decrease the anticancer activity of these compounds, presence of bromine atom at R-3 position and hydrophilic substitution at R-2 position are advantageous to the activity. Nucleophilic attack at atom number 14 is advantageous and electrophilic attack at atom number 15 is detrimental to anticancer activity. Atom number 2 is important and may be involved in dispersive interactions of the compounds with enzymes. The results offer an opportunity for further tailoring of these analogs for an active member. (C) 2008 Elsevier Masson SAS. All rights reserved.