5,6-tetramethylene-2-chloroisonicotinic acid | 203509-54-0

• 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: 5,6-tetramethylene-2-chloroisonicotinic acid
• 英文别名: 2-chloro-5,6,7,8-tetrahydroquinoline-4-carboxylic acid；2-Chloro-5,6,7,8-tetrahydroquinoline-4-carboxylic
• CAS: 203509-54-0
• 化学式: C₁₀H₁₀ClNO₂
• 分子量: 211.648
• InChiKey: WUBDWXBPUBGWLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-tetramethylene-2-chloroisonicotinic acid 在 氯化亚砜 、 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 2-chloro-N-(2-methoxyphenyl)-5,6,7,8-tetrahydroquinoline-4-carboxamide
  参考文献：
  名称：

  Synthesis and pharmacological activity of substituted amides of 2-chloro- and 2-arylamino-5,6-tri(tetra)methyleneisonicotinic acids

  摘要：

  DOI：

  10.1007/bf02508449
• 作为产物：
  描述：

  环己酮 在 乙醇 、 硫酸 、 sodium hydride 、 三氯氧磷 作用下， 反应 48.0h， 生成 5,6-tetramethylene-2-chloroisonicotinic acid
  参考文献：
  名称：

  Construction and functionalization of fused pyridine ring leading to novel compounds as potential antitubercular agents

  摘要：

  A series of fused and functionalized pyridine derivatives were designed, synthesized and tested for their potential antitubercular properties. All these novel compounds were prepared by using multistep methods involving the construction of pyridine ring as a key synthetic step. Some of these compounds were found to be interesting when tested for their antitubercular properties in vitro and one of them appeared as an attractive and potential antitubercular agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.096

文献信息

• Synthesis and pharmacological activity of isopropylamides of 2-arylamino-5,6,7,8-tetrahydroquinoline-4-carboxylic acids
  作者：T. A. Smirnova、M. Yu. Gavrilov、L. P. Drovosekova、F. Ya. Nazmetdinov、V. E. Kolla、M. E. Kon'shin

  DOI：10.1007/bf02464664

  日期：1997.3

  -4-carboxylic acid, which were used as the initial compounds in the synthesis of 5,6,7,8-tetrahydroquinoline-4-carboxylic acid hydrazides expected to possess antituberculous activity [3]. The purpose of this work was to search for new antiinflammatory, analgesic, and anticonvulsive agents among a series of isopropylamides of 2-arylamino-5,6,7,8-tetrahydroquinoline-4-carboxylic acids.

  如前所述，2-芳基氨基-5,6,7,8四氢喹啉-3-羧酸酰胺具有抗炎和镇痛活性 [1]。据报道，2-苯胺基辛可宁酸的取代酰胺具有相同类型的活性[2]。结构上与这些化合物类似的 5,6,7,8-四氢喹啉-4-羧酸衍生物尚未得到表征。仅报告了 2-oxo-1,2,5,6,7,8-haxahydroquinoline-4- 羧酸 (I) 和 2-chloro5,6,7,8-tetrahydroquinoline-4- 甲酯的一些数据羧酸，其被用作合成 5,6,7,8-四氢喹啉-4-羧酸酰肼的初始化合物，预计具有抗结核活性 [3]。这项工作的目的是寻找新的抗炎、镇痛、
• Synthesis and antibacterial activity of 2-arylidene- and 2-(5-nitrofurfurylidene)hydrazides of 2-chloro- and 2-arylamino-5,6-trimethylene and 5,6-tetramethyleneisonicotinic acids
  作者：T. A. Smirnova、M. Yu. Gavrilov、É. V. Voronina、M. E. Kon'shin

  DOI：10.1007/bf02464164

  日期：1998.2

  5-nitrofurfurylidenehydrazides of 2-chloroand 2-arylamino-5,6tri(tetra)methyleneisonicotinic acids The initial compounds were methyl ester [2] and ethyl esters ( I a Ic ) obtained by successive reactions of 5,6trimethylene and 5,6-tetramethylene-2-hydroxyisonicotinic acids with phosphorus pentachloride and the corresponding alcohol. The previous investigation showed that halogen atoms in the esters Ib were

  此前，我们报道了一系列 2-芳基氨基 5,6,7,8-四氢喹啉-4-羧酸的异丙基酰胺的合成和表征，具有抗炎和镇痛活性 [1]。此类的另一种活性化合物是 5,6,7,8-四氢喹啉 4-羧基酰肼，已知具有抗结核特性 [2]。这项工作的目的是在 2-氯和 2-芳氨基-5,6 三（四）亚甲基异烟酸的亚芳基和 5-硝基呋喃基酰肼中寻找具有抗菌活性的化合物 最初的化合物是甲酯 [2] 和乙酯（ I a Ic ) 通过 5,6 三亚甲基和 5,6-四亚甲基-2-羟基异烟酸与五氯化磷和相应的醇的连续反应获得。先前的研究表明，在 DMF 中沸腾 4 17 小时期间，酯 Ib 中的卤素原子不会被芳基氨基亲核置换（我们报道了 2-氯-5,6,7,8-四氢喹啉的低迁移率- 4-羧酸异丙基酰胺）[1]。该反应仅通过将这些酯与芳胺盐酸盐在无水丁醇中煮沸 12 小时进行，导致 2-芳氨基-5,6,7,8-四氢喹啉-4 羧酸酯
• Synthesis and pharmacological activity of 2-arylamino-5,6-tri(tetra)methyleneisonicotinic acid amides
  作者：T. A. Smirnova、M. Yu. Gavrilov、F. Ya. Nazmetdinov、L. P. Drovosekova、M. E. Kon'shin、V. E. Kolla

  DOI：10.1007/bf02509937

  日期：1999.4
• Construction and functionalization of fused pyridine ring leading to novel compounds as potential antitubercular agents
  作者：Balakrishna Dulla、Baojie Wan、Scott G. Franzblau、Ravikumar Kapavarapu、Oliver Reiser、Javed Iqbal、Manojit Pal

  DOI：10.1016/j.bmcl.2012.05.096

  日期：2012.7

  A series of fused and functionalized pyridine derivatives were designed, synthesized and tested for their potential antitubercular properties. All these novel compounds were prepared by using multistep methods involving the construction of pyridine ring as a key synthetic step. Some of these compounds were found to be interesting when tested for their antitubercular properties in vitro and one of them appeared as an attractive and potential antitubercular agent. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and pharmacological activity of substituted amides of 2-chloro- and 2-arylamino-5,6-tri(tetra)methyleneisonicotinic acids
  作者：T. A. Smirnova、M. Yu. Gavrilov、F. Ya. Nazmetdinov、L. P. Drovosekova、M. E. Kon'shin、V. E. Kolla

  DOI：10.1007/bf02508449

  日期：1999.3