1,2,3,4-Tetrahydroquinoline-6-sulfonyl chloride | 1314774-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,2,3,4-Tetrahydroquinoline-6-sulfonyl chloride
• 英文别名: 1,2,3,4-tetrahydroquinoline-6-sulfonyl chloride
• CAS: 1314774-11-2
• 化学式: C₉H₁₀ClNO₂S
• 分子量: 231.703
• InChiKey: ZCZUJRAHBKPOGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,3,4-Tetrahydroquinoline-6-sulfonyl chloride 、 2-Methoxy-4-phenyl-4,5-dihydro-1H-imidazole 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以100%的产率得到6-(2-methoxy-4-phenyl-4,5-dihydroimidazol-1-ylsulfonyl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Structure–activity relationship studies of novel arylsulfonylimidazolidinones for their anticancer activity

  摘要：

  To define the SAR, a series of novel N-arylsulfonylimidazolidinone derivatives were evaluated for their in vitro anticancer activity against five human tumor cell lines, including A549, COLO205, KATO III, K562, SK-OV-3 and murine leukemia (P288D1) cell line. Among them, N-(2-chloroacetyl)-6-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,4-dihydroquinoline-1(2H)-carboxamide (4m) and N-cyclohexyl-6-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,4-dihydroquinoline-1(2H)-carboxamide (4n) exhibited comparable in vitro anticancer activity to doxorubicin against A549, KATO III and K562 cell lines and gave superior xenographic results against NCI-H23 and SW620 cancer cell lines. Regarding the structure activity relationship, two critical points were discovered; the steric congestion at 4-position of N-arylsulfonylimidazolidinone scaffold abolishes the activity and the bulkiness or hydrophobicity of acyl groups at 3,4-dihydroquinoline of 4, especially with carbamoyl moiety, enormously enhances the activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.042

文献信息

• [EN] ACYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY<br/>[FR] COMPOSÉS ACYCLIQUES AYANT UNE AFFINITÉ POUR LE RÉCEPTEUR 5-HT6
  申请人：MEMORY PHARM CORP

  公开号：WO2010011546A2

  公开（公告）日：2010-01-28

  The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, R5, Q, G, Ar, m, and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
• Structure–activity relationship studies of novel arylsulfonylimidazolidinones for their anticancer activity
  作者：Santhosh Subramanian、Nam-Soo Kim、Pillaiyar Thanigaimalai、Vinay K. Sharma、Ki-Cheul Lee、Jong Seong Kang、Hwan-Mook Kim、Sang-Hun Jung

  DOI：10.1016/j.ejmech.2011.04.042

  日期：2011.8

  To define the SAR, a series of novel N-arylsulfonylimidazolidinone derivatives were evaluated for their in vitro anticancer activity against five human tumor cell lines, including A549, COLO205, KATO III, K562, SK-OV-3 and murine leukemia (P288D1) cell line. Among them, N-(2-chloroacetyl)-6-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,4-dihydroquinoline-1(2H)-carboxamide (4m) and N-cyclohexyl-6-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,4-dihydroquinoline-1(2H)-carboxamide (4n) exhibited comparable in vitro anticancer activity to doxorubicin against A549, KATO III and K562 cell lines and gave superior xenographic results against NCI-H23 and SW620 cancer cell lines. Regarding the structure activity relationship, two critical points were discovered; the steric congestion at 4-position of N-arylsulfonylimidazolidinone scaffold abolishes the activity and the bulkiness or hydrophobicity of acyl groups at 3,4-dihydroquinoline of 4, especially with carbamoyl moiety, enormously enhances the activity. (C) 2011 Elsevier Masson SAS. All rights reserved.