2,4-dimethyl-8-(2'-nitrophenyl)quinoline | 123730-14-3

• 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: 2,4-dimethyl-8-(2'-nitrophenyl)quinoline
• 英文别名: 2,4-dimethyl-8-(2-nitrophenyl)-quinoline；2,4-Dimethyl-8-(2-nitrophenyl)quinoline
• CAS: 123730-14-3
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: JKFALHJEPHKKLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-8-(2'-nitrophenyl)quinoline 在 高氯酸 、 亚磷酸三乙酯 作用下， 以 溶剂黄146 为溶剂， 反应 72.0h， 生成 4,6-dimethyl-6aλ⁵,7-diazabenzanthracen-6a-ium perchlorate
  参考文献：
  名称：

  Ollis, W. David; Stanforth, Stephen P.; Ramsden, Christopher A., Journal of the Chemical Society. Perkin transactions I, 1989, # 5, p. 953 - 956

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-硝基苯基)苯胺 在 calcium sulfate 、 硫酸 作用下， 反应 32.0h， 生成 2,4-dimethyl-8-(2'-nitrophenyl)quinoline
  参考文献：
  名称：

  Ollis, W. David; Stanforth, Stephen P.; Ramsden, Christopher A., Journal of the Chemical Society. Perkin transactions I, 1989, # 5, p. 953 - 956

  摘要：

  DOI：

文献信息

• [EN] CRF ANTAGONISTIC QUINO- AND QUINAZOLINES<br/>[FR] QUINO- ET QUINAZOLINES ANTAGONISTES CRF
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：WO1998047874A1

  公开（公告）日：1998-10-29

  (EN) This invention concerns compounds of formula (I), including the stereoisomers and the pharmaceutically acceptable acid addition salt forms thereof, wherein R1 is C1-6alkyl, NR6R7, OR6 or SR7; R2 is hydrogen, C1-6alkyl, C1-6alkyloxy or C1-6alkylthio; R3 is Ar1 or Het1; R4 and R5 are each independently selected from hydrogen, halo, C1-6alkyl, C1-6alkyloxy, trifluoromethyl, cyano, nitro, amino, and mono- or di(C1-6alkyl)amino; R6 is hydrogen, C1-6alkyl, C1-6alkylsulfonyl, C1-6alkylsulfoxy or C1-6alkylthio; R7 is hydrogen, C1-8alkyl, mono- or di(C3-6cycloalkyl)methyl, C3-6cycloalkyl, C3-6alkenyl, hydroxyC1-6alkyl, C1-6alkylcarbonyloxy-C1-6alkyl or C1-6alkyloxyC1-6alkyl; R6 is C1-8alkyl, mono- or di(C3-6cycloalkyl)-methyl, Ar2CH2, C1-6alkyloxyC1-6alkyl, hydroxyC1-6alkyl, C3-6alkenyl, thienylmethyl, furanylmethyl, C1-6alkylthioC1-6alkyl, mono- or di(C1-6alkyl)aminoC1-6alkyl, di(C1-6alkyl)amino, C1-6alkylcarbonylC1-6alkyl; or R6 and R7 taken together with the nitrogen atom to which they are attached may form a pyrrolidinyl, piperidinyl, homopiperidinyl or morpholinyl group, optionally substituted with C1-6alkyl or C1-6alkyloxyC1-6alkyl; and Ar1 and Ar2 are each optionally substituted phenyl; and Het1 is optionally substituted pyridinyl; having CRF receptor antagonistic properties; pharmaceutical compositions containing such compounds as active ingredients; methods of treating disorders related to hypersecretion of CRF such as depression, anxiety, substance abuse, by administering an effective amount of a compound of formula (I).(FR) La présente invention concerne des composés représentés par la formule (I) comprenant des stéréoisomères et les formes de sels d'addition acides pharmaceutiquement acceptables de ceux-ci, dans laquelle R1 représente C1-6alkyle, NR6R7, OR6 ou SR7; R2 représente hydrogène, C1-6alkyle, C1-6alkyloxy ou C1-6alkylthio; R3 représente Ar1 or Het1; R4 et R5 sont chacun sélectionnés indépendamment dans le groupe hydrogène, halo, C1-6alkyle, C1-6alkyloxy, trifluorométhyl, cyano, nitro, amino, et mono- ou di(C1-6alkyle)amino; R6 représente hydrogène, C1-6alkyle, C1-6alkylsulfonyl, C1-6alkylsulfoxy ou C1-6alkylthio; R7 représente hydrogène, C1-8alkyle, mono- ou di(C3-6cyclo-alkyle)méthyl, C3-6cycloalkyl, C3-6alcényl, hydroxyC1-6alkyle, C1-6alkylcarbonyloxyC1-6alkyle ou C1-6alkyloxyC1-6alkyle; R6 représente C1-8alkyle, mono- ou di(C3-6cycloalkyl)-méthyl, Ar2CH2, C1-6alkyloxyC1-6alkyle, hydroxyC1-6alkyle, C3-6alcényle, thiénylméthyl, furanylméthyl, C1-6alkylthioC1-6alkyle, mono ou di(C1-6alkyle)aminoC1-6alkyle, di(C1-6alkyle)amino, C1-6alkylcarbonylC1-6alkyle; ou R6 et R7 pris ensemble avec l'atome d'azote auquel ils sont liés peuvent former un pyrrolidinyl, un pipéridinyl, un homopipéridinyl ou un groupe morpholinyl, éventuellement substitué avec C1-6alkyle ou C1-6alkyloxyC1-6alkyle; et Ar1 et Ar2 représentent chacun un phényl éventuellement substitué; Het1 représente un pyridinyl éventuellement substitué; présentant des propriétés antagonistes de récepteur CFR. La présente invention concerne également des compositions pharmaceutiques contenant lesdits composés comme ingrédients actifs ainsi que des procédés de traitement d'affections liées à l'hypersécrétion de CRF telles que la dépression, l'anxiété, l'abus de substance, en administrant une quantité efficace d'un composé représenté par la formule (I).

  本发明涉及化合物(I)的公式，包括其立体异构体和药学上可接受的酸加成盐形式，其中R1为C1-6烷基，NR6R7，OR6或SR7; R2为氢，C1-6烷基，C1-6烷氧基或C1-6烷硫基; R3为Ar1或Het1; R4和R5各自独立地选择自氢，卤素，C1-6烷基，C1-6烷氧基，三氟甲基，氰基，硝基，氨基和单个或双(C1-6烷基)氨基; R6为氢，C1-6烷基，C1-6烷基磺酰基，C1-6烷氧基或C1-6烷硫基; R7为氢，C1-8烷基，单个或双(C3-6环烷基)甲基，C3-6环烷基，C3-6烯基，羟基C1-6烷基，C1-6烷基羧酸酯-C1-6烷基或C1-6烷氧基C1-6烷基; R6为C1-8烷基，单个或双(C3-6环烷基)-甲基，Ar2CH2，C1-6烷氧基C1-6烷基，羟基C1-6烷基，C3-6烯基，噻吩基甲基，呋喃基甲基，C1-6烷硫基C1-6烷基，单个或双(C1-6烷基)氨基C1-6烷基，双(C1-6烷基)氨基，C1-6烷基羰基C1-6烷基; 或R6和R7与它们连接的氮原子一起可以形成一个吡咯烷基，哌嗪基，同源哌嗪基或吗啡啉基，可选地取代C1-6烷基或C1-6烷氧基C1-6烷基; Ar1和Ar2各自为可选取代的苯基; Het1为可选取代的吡啶基; 具有CRF受体拮抗作用; 包含这样的化合物作为活性成分的药物组合物; 通过给予公式(I)化合物的有效量来治疗与CRF过度分泌相关的疾病，如抑郁症、焦虑症、物质滥用的方法。
• CRF antagonistic quino- and quinazolines
  申请人：Neurocrine Biosciences, Inc.

  公开号：US20040121998A1

  公开（公告）日：2004-06-24

  This invention concerns compounds of formula 1 including the stereoisomers and the pharmaceutically acceptable acid addition salt forms thereof, wherein R 1 is C 1-6 alkyl, NR 6 R 7 , OR 6 or SR 7 ; R 2 is hydrogen, C 1-6 alkyl, C 1-6 alkyloxy or C 1-6 alkylthio; R 3 is Ar 1 or Het 1 ; R 4 and R 5 are each independently selected from hydrogen, halo, C 1-6 alkyl, C 1-6 alkyloxy, trifluoromethyl, cyano, nitro, amino, and mono- or di(C 1-6 alkyl)amino; R 6 is hydrogen, C 1-6 alkyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfoxy or C 1-6 alkylthio; R 7 is hydrogen, C 1-8 alkyl, mono- or di(C 3-6 cyclo-alkyl)methyl, C 3-6 cycloalkyl, C 3-6 alkenyl, hydroxyC 1-6 alkyl, C 1-6 alkylcarbonyloxy-C 1-6 alkyl or C 1-6 alkyloxyC 1-6 alkyl; R 6 is C 1-8 alkyl, mono- or di(C 3-6 cycloalkyl)-methyl, Ar 2 CH 2 , C 1-6 alkyloxyC 1-6 alkyl, hydroxyC 1-6 alkyl, C 3-6 alkenyl, thienylmethyl, furanylmethyl, C 1-6 alkylthioC 1-6 alkyl, mono- or di(C 1-6 alkyl)aminoC 1-6 alkyl, di(C 1-6 alkyl)amino, C 1-6 alkylcarbonylC 1-6 alkyl; or R 6 and R 7 taken together with the nitrogen atom to which they are attached may form a pyrrolidinyl, piperidinyl, homopiperidinyl or morpholinyl group, optionally substituted with C 1-6 alkyl or C 1-6 alkyloxyC 1-6 alkyl; and Ar 1 and Ar 2 are each optionally substituted phenyl; and Het 1 is optionally substituted pyridinyl; having CRF receptor antagonistic properties; pharmaceutical compositions containing such compounds as active ingredients; methods of treating disorders related to hypersecretion of CRF such as depression, anxiety, substance abuse, by administering an effective amount of a compound of formula (I).

  本发明涉及式1的化合物，包括其立体异构体和药学上可接受的酸加成盐形式，其中R1是C1-6烷基，NR6R7，OR6或SR7; R2是氢，C1-6烷基，C1-6烷氧基或C1-6烷基硫基; R3是Ar1或Het1; R4和R5各自独立地选自氢，卤素，C1-6烷基，C1-6烷氧基，三氟甲基，氰基，硝基，氨基，和单烷基或双烷基（C1-6）氨基; R6是氢，C1-6烷基，C1-6烷基磺酰基，C1-6烷基亚磺酰基或C1-6烷基硫基; R7是氢，C1-8烷基，单烷基或双（C3-6）环烷基甲基，C3-6环烷基，C3-6烯基，羟基C1-6烷基，C1-6烷基羧酸酯-C1-6烷基或C1-6烷氧基C1-6烷基; R6是C1-8烷基，单烷基或双（C3-6）环烷基甲基，Ar2CH2，C1-6烷氧基C1-6烷基，羟基C1-6烷基，C3-6烯基，噻吩甲基，呋喃甲基，C1-6烷基硫基C1-6烷基，单烷基或双（C1-6）氨基C1-6烷基，双（C1-6）氨基，C1-6烷基羧酰基C1-6烷基; 或R6和R7与它们连接的氮原子一起可以形成吡咯烷基，哌啶基，同型哌啶基或吗啉基，可选地取代C1-6烷基或C1-6烷氧基C1-6烷基; Ar1和Ar2各自是可选地取代的苯基; Het1是可选地取代的吡啶基; 具有CRF受体拮抗性能的制剂，包含这样的化合物作为活性成分; 通过给予式（I）化合物的有效量来治疗与CRF的过度分泌相关的疾病，例如抑郁症，焦虑症，物质滥用等的方法。
• CRF antagonistic quino-and quinazolines
  申请人：——

  公开号：US20030119818A1

  公开（公告）日：2003-06-26

  This invention concerns compounds of formula 1 including the stereoisomers and the pharmaceutically acceptable acid addition salt forms thereof, wherein R 1 is C 1-6 alkyl, NR 6 R 7 , OR 6 or SR 7 ; R 2 is hydrogen, C 1-6 alkyl, C 1-6 alkyloxy or C 1-6 alkylthio; R 3 is Ar 1 or Het 1 ; R 4 and R 5 are each independently selected from hydrogen, halo, C 1-6 alkyl, C 1-6 alkyloxy, trifluoromethyl, cyano, nitro, amino, and mono- or di(C 1-6 alkyl)amino; R 6 is hydrogen, C 1-6 alkyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfoxy or C 1-6 alkylthio; R 7 is hydrogen, C 1-8 alkyl, mono- or di(C 3-6 cyclo-alkyl)methyl, C 3-6 cycloalkyl, C 3-6 alkenyl, hydroxyC 1-6 alkyl, C 1-6 alkylcarbonyloxy-C 1-6 alkyl or C 1-6 alkyloxyC 1-6 alkyl; R 6 is C 1-8 alkyl, mono- or di(C 3-6 cycloalkyl)-methyl, Ar 2 CH 2 , C 1-6 alkyloxyC 1-6 alkyl, hydroxyC 1-6 alkyl, C 3-6 alkenyl, thienylmethyl, furanylmethyl, C 1-6 alkylthioC 1-6 alkyl, mono- or di(C 1-6 alkyl)aminoC 1-6 alkyl, di(C 1-6 alkyl)amino, C 1-6 alkylcarbonylC 1-6 alkyl; or R 6 and R 7 taken together with the nitrogen atom to which they are attached may form a pyrrolidinyl, piperidinyl, homopiperidinyl or morpholinyl group, optionally substituted with C 1-6 alkyl or C 1-6 alkyloxyC 1-6 alkyl; and Ar 1 and Ar 2 are each optionally substituted phenyl; and Het 1 is optionally substituted pyridinyl; having CRF receptor antagonistic properties; pharmaceutical compositions containing such compounds as active ingredients; methods of treating disorders related to hypersecretion of CRF such as depression, anxiety, substance abuse, by administering an effective amount of a compound of formula (I).

  本发明涉及公式1的化合物，包括其立体异构体和药学上可接受的酸加成盐形式，其中R1是C1-6烷基，NR6R7，OR6或SR7；R2是氢，C1-6烷基，C1-6烷氧基或C1-6烷硫基；R3是Ar1或Het1；R4和R5各自独立地选自氢，卤素，C1-6烷基，C1-6烷氧基，三氟甲基，氰基，硝基，氨基，以及单烷基或二烷基氨基的C1-6；R6是氢，C1-6烷基，C1-6烷基磺酰基，C1-6烷基磺酸氧基或C1-6烷基硫基；R7是氢，C1-8烷基，单烷基或二(C3-6环烷基)甲基，C3-6环烷基，C3-6烯基，羟基C1-6烷基，C1-6烷基羧酸酯-C1-6烷基或C1-6烷氧基C1-6烷基；R6是C1-8烷基，单烷基或二(C3-6环烷基)-甲基，Ar2CH2，C1-6烷氧基C1-6烷基，羟基C1-6烷基，C3-6烯基，噻吩基甲基，呋喃基甲基，C1-6烷硫基C1-6烷基，单烷基或二烷基氨基C1-6烷基，二烷基氨基，C1-6烷基羧酰基C1-6烷基；或R6和R7连同它们所连接的氮原子可以形成吡咯烷基，哌啶基，同型哌啶基或吗啉基，可选择地用C1-6烷基或C1-6烷氧基C1-6烷基取代；Ar1和Ar2各自是可选择地取代的苯基；Het1是可选择地取代的吡啶基；具有CRF受体拮抗作用；含有这种化合物作为活性成分的药物组合物；通过给予公式(I)化合物的有效量治疗与CRF过度分泌相关的疾病，例如抑郁症，焦虑症，物质滥用。
• OLLIS, W. DAVID;STANFORTH, STEPHEN P.;RAMSDEN, CHRISTOPHER A., J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 953-956
  作者：OLLIS, W. DAVID、STANFORTH, STEPHEN P.、RAMSDEN, CHRISTOPHER A.

  DOI：——

  日期：——
• CRF ANTAGONISTIC QUINO- AND QUINAZOLINES
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0977737A1

  公开（公告）日：2000-02-09