1,2,3,4-四氢-1,4,4-三甲基-6-喹啉甲醛 | 179406-36-1

• 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: 1,2,3,4-四氢-1,4,4-三甲基-6-喹啉甲醛
• 英文名称: 1,4,4-trimethyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde
• 英文别名: 1,4,4-trimethyl-2,3-dihydroquinoline-6-carbaldehyde
• CAS: 179406-36-1
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: AAXGKLGYVGGLIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-四氢-1,4,4-三甲基-6-喹啉甲醛 在 四甲基乙二胺 、 仲丁基锂 、 sulfur 、 三乙胺 、 三氟乙酸酐 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.67h， 生成 9-(dimethylamino)-1,4,4-trimethyl-3,4-dihydro-1H-thiochromeno[3,2-g]quinolin-6(2H)-one
  参考文献：
  名称：

  Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1)

  摘要：

  Twelve thiorhodamine derivatives have been examined for their ability to stimulate the ATPase activity of purified human P-glycoprotein (P-gp)-His(10), to promote uptake of calcein AM and vinblastine into multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their rates of transport in monolayers of multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells. The thiorhodamine derivatives have structural diversity from amide and thioamide functionality (N,N-diethyl and N-piperidyl) at the 5-position of a 2-thienyl substituent on the thiorhodamine core and from diversity at the 3-amino substituent with N, N-dimethylamino, fused azadecalin (julolidyl), and fused N-methylcyclohexylamine (half-julolidyl) substituents. The julolidyl and half-julolidyl derivatives were more effective inhibitors of P-gp than the dimethylamino analogues. Amide-containing derivatives were transported much more rapidly than thioamide-containing derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.075
• 作为产物：
  描述：

  N-(3-methylbut-2-enyl)-N-methylaniline 在 硫酸 、 三氯氧磷 作用下， 反应 2.0h， 生成 1,2,3,4-四氢-1,4,4-三甲基-6-喹啉甲醛
  参考文献：
  名称：

  Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1)

  摘要：

  Twelve thiorhodamine derivatives have been examined for their ability to stimulate the ATPase activity of purified human P-glycoprotein (P-gp)-His(10), to promote uptake of calcein AM and vinblastine into multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their rates of transport in monolayers of multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells. The thiorhodamine derivatives have structural diversity from amide and thioamide functionality (N,N-diethyl and N-piperidyl) at the 5-position of a 2-thienyl substituent on the thiorhodamine core and from diversity at the 3-amino substituent with N, N-dimethylamino, fused azadecalin (julolidyl), and fused N-methylcyclohexylamine (half-julolidyl) substituents. The julolidyl and half-julolidyl derivatives were more effective inhibitors of P-gp than the dimethylamino analogues. Amide-containing derivatives were transported much more rapidly than thioamide-containing derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.075

文献信息

• Mono-or polyenic carboxylic acid derivatives
  申请人：Eisai Co., Ltd.

  公开号：US05977125A1

  公开（公告）日：1999-11-02

  Compounds of the formula ##STR1## and compounds of the formula ##STR2## or their salts have the potent ability to bind to retinoic acid receptors thus useful in treating psoriasis and rheumatoid arthritis.

  公式为##STR1##的化合物和公式为##STR2##的化合物或它们的盐具有与视黄酸受体结合的强大能力，因此在治疗牛皮癣和类风湿性关节炎方面非常有用。
• Heterocycle-containing carboxylic acid derivative and drug containing the same
  申请人：Eisai Co. Ltd.

  公开号：US20020032202A1

  公开（公告）日：2002-03-14

  Described is a heterocycle-containing carboxylic acid derivative represented by the following formula (I): 1 wherein A represents, for example, a heteroaryl group which contains at least one nitrogen atom and may have a substituent, B represents, for example, a heteroarylene group, a —CONH— group or a group represented by the formula —CR 6 ═CR 7 — in which R 6 and R 7 represents H, a lower alkyl group or the like, D represents an arylene group, a heteroarylene group or the like, n1 stands for 0 or 1, M represents, for example, a hydroxyl group or a lower alkoxy group; or a physiologically acceptable salt thereof. As a retinoic-related compound replacing retinoic acid, it permits the provision of a preventive and/or therapeutic for various diseases.

  描述了一种含有杂环的羧酸衍生物，其化学式如下（I）：1其中A代表含有至少一个氮原子和可能具有取代基的杂芳基团，B代表例如杂芳烷基团，—CONH—基团或由公式—CR6═CR7—所表示的基团，其中R6和R7代表H、低碳基团或类似物，D代表芳基团、杂芳基团或类似物，n1代表0或1，M代表例如羟基或低碳氧基团；或其生理上可接受的盐。作为替代视黄酸的视黄酸相关化合物，它可以提供预防和/或治疗各种疾病的方法。
• Heterocycl-containing carboxylic acid derivative and drug containing the same
  申请人：Eisai Co. Ltd.

  公开号：US20020103234A1

  公开（公告）日：2002-08-01

  Described is a heterocycle-containing carboxylic acid derivative represented by the following formula (I): 1 wherein A represents, for example, a heteroaryl group which contains at least one nitrogen atom and may have a substituent, B represents, for example, a heteroarylene group, a —CONH— group or a group represented by the formula —CR 6 ═CR 7 — in which R 6 and R 7 represents H, a lower alkyl group or the like, D represents an arylene group, a heteroarylene group or the like, n1 stands for 0 or 1, M represents, for example, a hydroxyl group or a lower alkoxy group; or a physiologically acceptable salt thereof. As a retinoic-related compound replacing retinoic acid, it permits the provision of a preventive and/or therapeutic for various diseases.

  描述了一种含杂环的羧酸衍生物，其化学式为（I）：1，其中A代表例如至少含有一个氮原子并且可能具有取代基的杂芳基团，B代表例如杂芳烃基团，-CONH-基团或由式子-CR6═CR7-表示的基团，其中R6和R7代表H、低碳基或类似物，D代表芳烃基团、杂芳烃基团或类似物，n1代表0或1，M代表例如羟基或低碳氧基基团；或其生理上可接受的盐。作为替代视黄酸的视黄酸相关化合物，它可以提供预防和/或治疗各种疾病的方法。
• MONO- OR POLYENIC CARBOXYLIC ACID DERIVATIVE
  申请人：Eisai Co., Ltd.

  公开号：EP0790228A1

  公开（公告）日：1997-08-20

  To provide novel compounds relating to retinoid which can substitute for retinoic acid used for preventing and treating several diseases and having antagonism against retinoid. Heterocyclic compounds represented by the general formula (1-I) or physiologically acceptable salts thereof:         Z-(CR3=CR2)n-COOR1     (1-I) Compounds represented by the general formula (2-I) or physiologically acceptable salts thereof: The compounds according to the present invention exhibit extremely high ability to bind RARs and are effective for treating various kind of diseases such as abnormality in cornification and rheumatoid arthritis.

  提供与维甲酸有关的新型化合物，这些化合物可以替代用于预防和治疗多种疾病的维甲酸，并对维甲酸具有拮抗作用。 通式（1-I）代表的杂环化合物或其生理上可接受的盐类： Z-(CR3=CR2)n-COOR1 (1-I) 通式 (2-I) 所代表的化合物或其生理学上可接受的盐： 本发明的化合物具有极高的结合 RARs 的能力，可有效治疗各种疾病，如玉米粒化异常和类风湿性关节炎。
• HETEROCYCLIC CARBOXYLIC ACID DERIVATIVES AND DRUGS CONTAINING THE SAME
  申请人：Eisai Co., Ltd.

  公开号：EP0838453A1

  公开（公告）日：1998-04-29

  Described is a heterocycle-containing carboxylic acid derivative represented by the following formula (I): wherein A represents, for example, a heteroaryl group which contains at least one nitrogen atom and may have a substituent, B represents, for example, a heteroarylene group, a -CONH- group or a group represented by the formula -CR6=CR7- in which R6 and R7 represents H, a lower alkyl group or the like, D represents an arylene group, a heteroarylene group or the like, n1 stands for 0 or 1, M represents, for example, a hydroxyl group or a lower alkoxy group; or a physiologically acceptable salt thereof. As a retinoic-related compound replacing retinoic acid, it permits the provision of a preventive and/or therapeutic for various diseases.

  所述的是由下式(I)代表的含杂环的羧酸衍生物： 其中 A 代表例如含有至少一个氮原子并可具有取代基的杂芳基，B 代表例如杂芳基、-CONH- 基团或由式 -CR6=CR7- 代表的基团，其中 R6 和 R7 代表 H、低级烷基或类似基团，D 代表芳基、杂芳基或类似基团，n1 代表 0 或 1，M 代表例如羟基或低级烷氧基；或其生理学上可接受的盐。作为替代维甲酸的维甲酸相关化合物，它可以预防和/或治疗各种疾病。