4-氯喹啉-7-羧酸酰胺 | 178984-42-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 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
• 中文名称: 4-氯喹啉-7-羧酸酰胺
• 英文名称: 7-Carbamoyl-4-chloroquinoline
• 英文别名: 4-chloroquinoline-7-carboxylic acid amide；4-Chloroquinoline-7-carboxamide
• CAS: 178984-42-4
• 化学式: C₁₀H₇ClN₂O
• 分子量: 206.631
• InChiKey: FIMOQXLNZMESNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氯喹啉-7-羧酸酰胺 在 ammonium hydroxide 、 zinc(II) chloride 作用下， 以40%的产率得到4-aminoquinolin-7-carboxamide
  参考文献：
  名称：

  Structure–activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods

  摘要：

  In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (logK) and inhibition of beta-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, logK values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (pi) of the group X. The logK values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% beta-hematin inhibitory activity (log BHIA(50)) was found to correlate with logK and either meta (sigma(m)) or para (sigma(p)) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that logK values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of beta-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.040
• 作为产物：
  描述：

  3-氨基苯甲酰胺 在 三氯氧磷 作用下， 以 二苯醚 、 乙醇 为溶剂， 反应 2.58h， 生成 4-氯喹啉-7-羧酸酰胺
  参考文献：
  名称：

  Structure–activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods

  摘要：

  In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (logK) and inhibition of beta-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, logK values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (pi) of the group X. The logK values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% beta-hematin inhibitory activity (log BHIA(50)) was found to correlate with logK and either meta (sigma(m)) or para (sigma(p)) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that logK values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of beta-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.040

文献信息

• [EN] QUINOLINE EZH2 INHIBITORS<br/>[FR] INHIBITEURS QUINOLÉINE D'EZH2
  申请人：BAYER PHARMA AG

  公开号：WO2017025493A1

  公开（公告）日：2017-02-16

  The present invention relates to quinolines of general formula (I) to methods for their preparation, to intermediates for their preparation, to pharmaceutical compositions comprising at least one of those compounds, and to the use thereof.

  本发明涉及通式(I)的喹啉化合物，以及其制备方法、制备中间体、包含至少一种这些化合物的药物组合物，以及它们的用途。
• Aminoalcohol derivatives and their use as beta 3 adrenergic agonists
  申请人：Fujisawa Pharmaceutical Co. Ltd.

  公开号：US20020143034A1

  公开（公告）日：2002-10-03

  A compound of the formula (I): 1 wherein X 1 is bond or —OCH 2 —; X 2 is —(CH 2 ) n —, in which n is 1, 2 or 3; X 3 is bond, —O—, —S—, —OCH 2 —, or —NH—; R 1 is phenyl or pyridyl each of which may have one or two substituent(s) selected from the group consisting of hydroxy, halogen, etc.; R 2 is hydrogen, (lower)alkoxycarbonyl, etc.; R 3 is hydroxy(lower)alkyl; halo(lower)alkyl, etc.; R 4 is aryl or unsaturated heterocyclic group, each of which may have one or two substituent(s) selected from the group consisting of lower alkyl, hydroxy, carbamoyl, halogen, lower alkoxy, etc.; and a salt thereof which is useful as a medicament.

  该化合物的结构式如下：其中X1是化学键或—OCH2—；X2是—(CH2)n—，其中n为1、2或3；X3是化学键，—O—，—S—，—OCH2—或—NH—；R1是苯基或吡啶基，每个基上可能有一个或两个亚基，如羟基、卤素等；R2是氢、（低）烷氧羰基等；R3是羟基（低）烷基、卤代（低）烷基等；R4是芳基或不饱和杂环基，每个基上可能有一个或两个亚基，如低烷基、羟基、氨基甲酰基、卤素、低烷氧基等；以及其盐，可用作药物。
• QUINOLINE DERIVATIVES
  申请人：Jung Frederic Henri

  公开号：US20090076074A1

  公开（公告）日：2009-03-19

  The invention concerns quinoline derivatives of Formula I or a pharmaceutically-acceptable salt thereof, wherein each of X 1 , p, R 1 , q, R 2 , R 3 , R 4 , R 5 , Ring A, r and R 6 has any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the treatment of cell proliferative disorders.

  本发明涉及公式I的喹啉衍生物或其药学上可接受的盐，其中X1、p、R1、q、R2、R3、R4、R5、环A、r和R6中的每一个具有在本说明书中定义的任何含义；制备它们的过程，包含它们的制药组合物以及它们在制造用于治疗细胞增殖性疾病的药物的过程中的使用。
• THIOQUINOLONE DERIVATIVE
  申请人：ZENYAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0786454A1

  公开（公告）日：1997-07-30

  Disclosed is a thioquinolone derivative which exhibits highly selective antibacterial activity against Helicobacter pylori and which is represented by the formula I wherein R1 and R2 respectively represent hydrogen atom or R1 and R2 are joined to form ―O―(CH2)2-; R3 represents halogen atom, C1-C12 alkyl group, C1-C12 alkoxy group, lower alkylsulfonyloxy group, carboxy lower alkoxy group, lower alkylthio group, benzyloxy group, benzylthio group, phenoxy group, styryl group, nitro group, phenyl group, naphthyl group, piperazinyl group, morpholino group or hydroxyl group or represents ―CH2R5, ―COR6 or ―NR7R8 wherein R5 represents benzyl group, phenyl group, hydroxyl group, lower alkoxy group, lower alkylcarbonyloxy group, phenoxy group, di-lower alkylamino group or benzimidazolylthio group, R6 represents lower alkyl group or amino group and R7 and R8 respectively represent lower alkyl group; and R4 represents hydrogen atom or lower alkyl group or is coupled with R3 to form cyclohexene ring, benzene ring or pyridine ring, R3 being not halogen atom at any of positions 5 to 8, methyl group at position 6 or methoxy group at position 6 of the quinoline ring when R1, R2 and R4 are respectively hydrogen atom, R3 and R4 being not at positions 6 and 7 or positions 6 and 8 of the quinoline ring when R1 and R2 are respectively hydrogen atom and R4 is lower alkyl group.

  本发明公开了一种硫代喹啉酮衍生物，它对幽门螺旋杆菌具有高选择性抗菌活性，由式 I 表示 其中 R1 和 R2 分别代表氢原子或 R1 和 R2 连接形成-O-(CH2)2-； R3代表卤素原子、C1-C12烷基、C1-C12烷氧基、低级烷基磺酰氧基、低级烷氧基羧基、低级烷硫基、苄氧基、苄硫基、苯氧基、苯乙烯基、硝基、苯基、萘基、哌嗪基、吗啉基或羟基或代表-CH2R5、-其中 R5 代表苄基、苯基、羟基、低级烷氧基、低级烷基羰氧基、苯氧基、二低级烷基氨基或苯并咪唑硫基，R6 代表低级烷基或氨基，R7 和 R8 分别代表低级烷基；和 R4 代表氢原子或低级烷基，或与 R3 结合形成环己烯环、苯环或吡啶环、 当 R1、R2 和 R4 分别为氢原子时，R3 不是喹啉环 5 至 8 位上的卤素原子、6 位上的甲基或 6 位上的甲氧基、 当 R1 和 R2 分别为氢原子和 R4 为低级烷基时，R3 和 R4 不在喹啉环的第 6 和 7 位或第 6 和 8 位。
• EP1724268
  申请人：——

  公开号：——

  公开（公告）日：——