6,7-dimethoxy-4-methyl-quinolin-2-ol | 88636-77-5

• 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: 6,7-dimethoxy-4-methyl-quinolin-2-ol
• 英文别名: 6,7-Dimethoxy-4-methyl-chinolin-2-ol；6,7-Dimethoxy-4-methyl-2-chinolinol；6,7-dimethoxy-4-methyl-1H-quinolin-2-one
• CAS: 88636-77-5
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: QLWBLPSNXJHNCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-4-methyl-quinolin-2-ol 在 palladium on activated charcoal 、 sodium acetate 、 溶剂黄146 、 三氯氧磷 作用下， 生成 6,7-二甲氧基-4-甲基喹啉
  参考文献：
  名称：

  THE SEARCH FOR SUPERIOR DRUGS FOR TROPICAL DISEASES. I. DERIVATIVES OF QUININALDEHYDE AND 6,7-DIMETHOXYCINCHONINALDEHYDE

  摘要：

  DOI：

  10.1021/jo01180a013
• 作为产物：
  描述：

  3,4-二甲氧基乙酰乙酰苯胺 在 硫酸 作用下， 以 水 为溶剂， 生成 6,7-dimethoxy-4-methyl-quinolin-2-ol
  参考文献：
  名称：

  Long-Wavelength-Absorbing and -Emitting Carbostyrils with High Fluorescence Quantum Yields

  摘要：

  Synthesis, absorption and fluorescence spectra, as well as quantum yields of a series of donor-acceptor-substituted carbostyrils (= quinolin-2(1H)-ones), are reported. Unprecedented strong absorption maxima (epsilon = 10000-20000) close to the visible spectrum, large Stokes shifts up to 130 nm, and quantum yields up to 0.7 are obtained with derivatives containing donor substituents at C(6) and C(7), and either one Ph substituent at C(3) or one CF3 residue at C(4). For analytical applications in biochemistry and medicine, N(1)-functionalization, or amidoacylation at C(3) in the case of the CF3 derivatives, is possible without a concomitant hypsochromic shift of their absorption and emission maxima. Semiempirical molecular-orbital calculations (AM1 for structures, ZINDO for electronic transition energies) prove to bit a suitable tool for the prediction of absorption properties of these compounds. The crystal-structure analysis of 6,7-dimethoxy-1-methyl-3-nitro-4-(trifluoromethyl)quinolin-2-(1H)-one (7) (C13H11F3N2O5, monoclinic, P2(1)/c, a = 12.372(2), b = 12.154(2), c = 10.119(2)Angstrom, beta = 112.95(2)degrees) shows that the NO2 group, squeezed between the CF3 and the C=O group, is oriented almost perpendicularly (87.8(4)degrees) to the ring plane. The intramolecular F ... N distance between the CF3 and the NO2 group is only 2.513(4)Angstrom.

  DOI：

  10.1002/(sici)1522-2675(19990908)82:9<1408::aid-hlca1408>3.0.co;2-q

文献信息

• BIHETEROCYCLIC COMPOUND
  申请人：SUMITOMO DAINIPPON PHARMA CO., LTD.

  公开号：US20190016711A1

  公开（公告）日：2019-01-17

  The present invention provides a compound of formula (1) and a pharmaceutical composition comprising the compound useful as a nerve regeneration promoter wherein R 1 -L- is R 1 —OC(O)—, or the like, R 1 is hydrogen atom, optionally-substituted C 1-6 alkyl group, optionally-substituted 3- to 8-membered cycloalkyl group, or the like, R 2 is hydrogen atom or the like, Ring A is formula (2) or formula (3) wherein R 3 is hydrogen atom, optionally-substituted C 1-6 alkyl group, or the like, the part of X, Y, and Z is X═Y—Z, X—Y═Z, or X—Y—Z, X is nitrogen atom, NR 4 (R 4 is hydrogen atom, optionally-substituted C 1-6 alkyl group, or the like), or the like, Y is carbon atom or the like, and Z is carbon atom, nitrogen atom or the like.

  本发明提供了一种具有式（1）的化合物和包括该化合物的药物组合物，其用作神经再生促进剂，其中R1-L-为R1—OC(O)—，或类似物，R1为氢原子，可选择取代的C1-6烷基基团，可选择取代的3-至8-成员环烷基基团，或类似物，R2为氢原子或类似物，环A为式（2）或式（3），其中R3为氢原子，可选择取代的C1-6烷基基团，或类似物，X、Y和Z的部分为X═Y—Z，X—Y═Z，或X—Y—Z，X为氮原子，NR4（R4为氢原子，可选择取代的C1-6烷基基团，或类似物），或类似物，Y为碳原子或类似物，Z为碳原子，氮原子或类似物。
• [EN] ECTONUCLEOTIDE PYROPHOSPHATASE-PHOSPHODIESTERASE-1 (ENPP1) INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS D'ECTONUCLÉOTIDE PYROPHOSPHATASE-PHOSPHODIESTÉRASE 1 (ENPP1) ET LEURS UTILISATIONS
  申请人：INTEGRAL BIOSCIENCES PRIVATE LTD

  公开号：WO2022091048A1

  公开（公告）日：2022-05-05

  The present invention discloses compounds useful in treatment of conditions associated with dysfunction of ectonucleotide pyrophosphatase / phosphodiesterase-1 (ENPP1) enzyme. Specifically, the present invention discloses compound of formula (J) which exhibit inhibitory activity against ENPP1. Method of treating conditions associated with over-expression of ENPP1 gene with such compound is disclosed. Uses thereof, pharmaceutical composition, and kits are also disclosed.

  本发明揭示了在治疗与外核苷酸焦磷酸酶/磷酸二酯酶-1 (ENPP1)酶功能障碍相关的疾病中有用的化合物。具体而言，本发明揭示了公式（J）的化合物，这些化合物表现出对ENPP1的抑制活性。揭示了使用这种化合物治疗与ENPP1基因过度表达相关的疾病的方法。还揭示了其用途、制药组合物和试剂盒。
• Biheterocyclic compound
  申请人：SUMITOMO DAINIPPON PHARMA CO., LTD.

  公开号：US10323024B2

  公开（公告）日：2019-06-18

  The present invention provides a compound of formula (1) and a pharmaceutical composition comprising the compound useful as a nerve regeneration promoter wherein R1-L- is R1—OC(O)—, or the like, R1 is hydrogen atom, optionally-substituted C1-6 alkyl group, optionally-substituted 3- to 8-membered cycloalkyl group, or the like, R2 is hydrogen atom or the like, Ring A is formula (2) or formula (3) wherein R3 is hydrogen atom, optionally-substituted C1-6 alkyl group, or the like, the part of X, Y, and Z is X═Y—Z, X—Y═Z, or X—Y—Z, X is nitrogen atom, NR4 (R4 is hydrogen atom, optionally-substituted C1-6 alkyl group, or the like), or the like, Y is carbon atom or the like, and Z is carbon atom, nitrogen atom or the like.

  本发明提供了一种式（1）化合物和一种包含该化合物的药物组合物，可用作神经再生促进剂 其中 R1-L- 是 R1-OC(O)- 或类似物，R1 是氢原子、任选取代的 C1-6 烷基、任选取代的 3 至 8 元环烷基或类似物，R2 是氢原子或类似物，环 A 是式 (2) 或式 (3)，其中 R3 是氢原子、X、Y 和 Z 的部分是 X═Y-Z、X-Y═Z 或 X-Y-Z，X 是氮原子、NR4（R4 是氢原子、任选取代的 C1-6 烷基或类似物）或类似物，Y 是碳原子或类似物，Z 是碳原子、氮原子或类似物。
• Ruthenium-Catalyzed Cyclization of Anilides with Substituted Propiolates or Acrylates: An Efficient Route to 2-Quinolinones
  作者：Rajendran Manikandan、Masilamani Jeganmohan

  DOI：10.1021/ol501548e

  日期：2014.7.3

  A Ru-catalyzed cyclization of anilides with propiolates or acrylates affording 2-quinolinones having diverse functional groups in good to excellent yields is described. Later, 2-quinolinones were converted into 3-halo-2-quinolinones and 2-chloroquinolines. The proposed mechanism was strongly supported by experimental evidence and deuterium labeling studies.
• Lions, Journal and Proceedings - Royal Society of New South Wales, 1938, vol. 71, p. 242,248
  作者：Lions

  DOI：——

  日期：——