2-(4'-methylbenzenesulfonyl)-L-glutamic acid dichloride | 108590-52-9

• 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-(4'-methylbenzenesulfonyl)-L-glutamic acid dichloride
• 英文别名: N-tosyl-L-glutamyl dichloride；N-(toluene-4-sulfonyl)-L-glutamoyl chloride；N-(Toluol-4-sulfonyl)-L-glutamoylchlorid；p-Toluenesulfonyl-glutamic acid di-chloride；(2S)-2-[(4-methylphenyl)sulfonylamino]pentanedioyl dichloride
• CAS: 108590-52-9
• 化学式: C₁₂H₁₃Cl₂NO₄S
• 分子量: 338.212
• InChiKey: LBKNGJSUHUEERP-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4'-methylbenzenesulfonyl)-L-glutamic acid dichloride 在 氯仿 、 氨 作用下， 生成 1-对甲苯磺酰基-5-氧代吡咯烷-2-甲酰胺
  参考文献：
  名称：

  1-p-Toluenesulfonyl-L-pyroglutamyl Chloride and 1-p-Toluenesulfonyl-L-glutamyl Dichloride in the Preparation of Glutamic Acid Derivatives¹

  摘要：

  DOI：

  10.1021/ja01574a030
• 作为产物：
  描述：

  L-谷氨酸 在 sodium hydroxide 、 氯化亚砜 作用下， 反应 0.5h， 生成 2-(4'-methylbenzenesulfonyl)-L-glutamic acid dichloride
  参考文献：
  名称：

  Syntheses, biological evaluation and QSAR study on antitumor activity of 1,5-N,N′-disubstituted-2-(substituted benzenesulphonyl) glutamamides

  摘要：

  We have reported [unpublished data] the synthesis and QSAR of 5-substituted-2-(substituted benzenesulphonyl) glutamines which have shown the importance of steric factor on the aliphatic chain. N-Phthalyl isoglutamine, having the substitution at position I of the glutamic acid moiety, is the metabolite of recently approved thalidomide For different types of tumors by US FDA, Based on these, 36 now 1,5-N,N'-disubstituted-2-(substituted benzenesulphonyl) glutamamides were synthesized, as tools for further elucidation of the structural requirements for antitumor activity. All the synthesized compounds were tested for antitumor activity against Ehrlich Ascites Carcinoma (EAC) in Swiss albino mice using tumor weight as inhibitory parameter. Quantitative structure-activity relationship (QSAR) studies of these analogues revealed that the electron donating groups on the phenyl ring are found to be mandatory for the activity which was also proved by the negative coefficient of indicator parameter I-3, for NO2 group on the phenyl ring. Molecular volume (MV) and steric factor at R-5 position also plays a role in ligand -receptor interactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00007-x

文献信息

• Antitumor agents: diazomethyl ketone and chloromethyl ketone analogs prepared from N-tosyl amino acids
  作者：Z. Sajadi、M. Kashani、L. J. Loeffler、I. H. Hall

  DOI：10.1021/jm00177a012

  日期：1980.3

  The N-tosyl diazomethyl ketone analogues synthesized from glycine, L-leucine, and L-proline were the most active of this series in the Ehrlich ascites screen, along with 5-keto-1-tosyl-2-(diazoacetyl)pyrrolidine and the diazomethyl ketone analogues prepared from 6-(N-tosylamino)caproic acid. In the P-388 lymphocytic leukemia screen, the N-tosyl chloromethyl ketone prepared from glycine and the compound

  已合成了由N-甲苯磺酰基氨基酸制得的重氮甲基酮和氯甲基酮类似物，并在小鼠艾氏腹水癌和P-388淋巴细胞白血病筛选中测试了其抗肿瘤活性。由甘氨酸，L-丙氨酸，β-丙氨酸，L-缬氨酸和6-（N-甲苯磺酰基-氨基）己酸制备的N-甲苯磺酰氯甲基酮类似物是Ehrlich腹水癌筛查中最有效的抗肿瘤药物。由甘氨酸，L-亮氨酸和L-脯氨酸合成的N-甲苯磺酰基重氮甲基酮类似物在Ehrlich腹水筛查中是该系列中最活跃的，同时还有5-酮基-1-甲苯磺酰基-2-（重氮乙酰基）吡咯烷和由6-（N-甲苯磺酰基氨基）己酸制得的重氮甲基酮类似物。在P-388淋巴细胞白血病屏幕中，
• Distress and disease status among patients with rheumatoid arthritis: Roles of coping styles and perceived responses from support providers
  作者：Kenneth W. Griffin、Ronald Friend、Alan T. Kaell、Ronald S. Bennett

  DOI：10.1207/s15324796abm2302_8

  日期：2001.5

  Previous research has shown that social support can have a beneficial impact on coping processes and psychological adjustment in patients with rheumatoid arthritis (RA). The association of individual coping styles and perceived responses from others to one's pain episodes with patients' distress and disease status over time was investigated. The sample consisted of 42 middle-aged patients with RA who were predominantly White (98%), female (64%), and married (88%). Participants completed surveys and their rheumatologist completed clinical assessments of patient disease status at 2 time points over a 9-month period Although punishing responses from others (e.g, getting irritated or angry when the patient is in pain) were perceived as relatively infrequent, they were associated with a patient coping style of focusing on and venting of negative emotion as well as elevated negative affect (NA). Findings also indicated that those who perceived punishing responses from close others and coped by venting negative emotions reported increased NA over time and were rated by their rheumatologist as having more severe RA disease status over time. Implications for psychosocial intervention and directions for future research are discussed.
• The Synthesis of L-Glutaminyl-L-asparagine, L-Glutamine and L-Isoglutamine from p-Toluenesulfonyl-L-glutamic Acid¹
  作者：John M. Swan、Vincent du Vigneaud

  DOI：10.1021/ja01641a002

  日期：1954.6