trimethyl 5-hydroxy-4-oxo-1,6-dihydropyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate | 102408-71-9

• 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: trimethyl 5-hydroxy-4-oxo-1,6-dihydropyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate
• 英文别名: 4,5-Dihydroxy-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester
• CAS: 102408-71-9
• 化学式: C₁₇H₁₄N₂O₈
• 分子量: 374.307
• InChiKey: FGHAMOSNRSVWSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  148.04
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  trimethyl 5-hydroxy-4-oxo-1,6-dihydropyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 以155 mg的产率得到
  参考文献：
  名称：

  吡咯喹啉醌衍生物或其可药用的盐、制备方法及用途

  摘要：

  本发明公开了如式(I)所示结构的吡咯喹啉醌衍生物或其可药用的盐、制备方法及用途。该类衍生物具有出色的溶解性和/或渗透性，显著优于PQQ及PQQ盐(市售二钠盐)，且在抗炎、抗糖尿病及抗代谢性疾病模型中表现出理想药效，优于PQQ及PQQ盐(市售二钠盐)本发明还提供所述衍生物及其中间体的制备方法、药物组合物及其医药用途。

  公开号：

  CN114805339A
• 作为产物：
  描述：

  4,5-二氧代-4,5-二氢-1H-吡咯[2,3-f]喹啉-2,7,9-三羧酸三甲酯 在 苯硫酚 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以80%的产率得到trimethyl 5-hydroxy-4-oxo-1,6-dihydropyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate
  参考文献：
  名称：

  Reaction of Reduced PQQ (PQQH₂) and Molecular Oxygen

  摘要：

  还原型 PQQ（PQQH2）是通过 PQQ 与苯硫酚、1-苄基-1,4-二氢烟酰胺（BNAH）、亚硫酸钠或硼氢化钠反应制备的。研究了分子氧在水溶液中将 PQQH2 氧化成 PQQ 的动力学过程。随着反应的进行，氧化速度逐渐加快，这可能是由于 PQQH2 和 O2 反应产生了 PQQH2 和 H2O2 的副反应。事实上，H2O2 的产率为 PQQH2 的 50%。初始速率与氧气浓度呈一阶关系。pH 值-速率曲线表明反应中的活性物种是 PQQH-。在这一反应中几乎检测不到 O2\ewdot 和 PQQ 本身的自催化作用。此外，还讨论了氧化的机理。

  DOI：

  10.1246/bcsj.59.1911

文献信息

• Biomimetic oxidation of alcohols by coenzyme PQQ-trimethyl ester
  作者：Shinobu Itoh、Minae Mure、Yoshiki Ohshiro、Toshio Agawa

  DOI：10.1016/s0040-4039(00)98998-6

  日期：1985.1

  Oxidation of alcohols to corresponding carbonyl compounds by coenzyme PQQ-trimethyl ester was performed in the presence of aluminum t-butoxide or aluminum chloride under anaerobic conditions. Reduced PQQTME (PQQTMEH2) was obtained by acidification of an aluminum complex of reduced PQQTME which was isolated in the reaction.

  在厌氧条件下，在叔丁醇铝或氯化铝的存在下，通过辅酶PQQ-三甲酯将醇氧化为相应的羰基化合物。通过酸化还原的PQQTME的铝络合物，在反应中分离得到还原的PQQTME（PQQTMEH 2）。
• Photochemical Reactions of Coenzyme PQQ (Pyrroloquinolinequinone) and Analogues with Benzyl Alcohol Derivatives via Photoinduced Electron Transfer
  作者：Shunichi Fukuzumi、Shinobu Itoh、Takashi Komori、Tomoyoshi Suenobu、Akito Ishida、Mamoru Fujitsuka、Osamu Ito

  DOI：10.1021/ja001351g

  日期：2000.9.1

  Photochemical redox reactions of the trimethyl ester of coenzyme PQQ (PQQTME) with benzyl alcohol derivatives (ArCH2OH), tetrahydrofuran, and 1,4-cyclohexadiene occur efficiently under visible light irradiation in MeCN to yield PQQTMEH2 (reduced PQQTME in the quinol form) and the corresponding dehydrogenated products (ArCHO, furan, and benzene) quantitatively. A similar photochemical oxidation of benzyl

  辅酶 PQQ 的三甲酯 (PQQTME) 与苯甲醇衍生物 (ArCH2OH)、四氢呋喃和 1,4-环己二烯在可见光照射下在 MeCN 中有效发生光化学氧化还原反应，生成 PQQTMEH2（还原的 PQQTME 以醌醇形式）和相应的脱氢产物（ArCHO、呋喃和苯）。苯甲醇的类似光化学氧化也发生在菲咯啉醌衍生物 (PTQ)、苯并喹啉醌衍生物 (BQQ) 和菲醌 (PQ) 中。PQQTME 和类似物在 MeCN 中基本上是无荧光的，并且在分子氧的存在下，邻醌的光化学反应会显着延迟。在 MeCN 溶液的激光闪光光解中检测到邻醌的三重激发态的瞬态吸收光谱。从 TT 光谱的衰减确定了邻醌的三重激发态的寿命。三重态激发的猝灭速率常数...
• Synthesis and characterization of the 6-deaza derivative of coenzyme PQQ, methyl 4,5-dihydro-4,5-dioxobenz[g]indole-2-carboxylate
  作者：Shinobu Itoh、Yoshifumi Fukui、Masaki Ogino、Shigenobu Haranou、Mitsuo Komatsu、Yoshiki Ohshiro

  DOI：10.1021/jo00036a007

  日期：1992.5

  The synthesis of the 6-deaza derivative of coenzyme PQQ, methyl 4,5-dihydro-4,5-dioxobenz[g]indole-2-carboxylate (4), is described, and its physical and chemical properties are compared to those of the trimethyl ester of PQQ (2) and the methyl ester of 7,9-didecarboxy PQQ (3). The synthesis of 4 was achieved by starting with 1-aminonaphthalene and constructing 2-carbomethoxybenz[g]indole (7) by a Japp-Klingemann reaction with methyl alpha-methylacetoacetate and a subsequent Fischer indolization reaction. The quinone function was introduced by a Fremy's salt oxidation of 5-aminoindole 9 which was prepared from 7 by regioselective nitration and catalytic hydrogenation. From the physical properties, it can be recognized that the peri pyridine nitrogen and the ester groups at the 7- and 9-positions considerably affect the electronic nature of the molecules. This is reflected on the reactivities of the quinones in the acetone-adduct formation, the reaction with phenylhydrazine, and the aerobic autorecycling oxidation of benzylamine. The significant roles of the pyridine nitrogen and the ester groups in these reactions are discussed.
• Mure, Minae; Nii, Kazumi; Inoue, Teruhisa, Journal of the Chemical Society. Perkin transactions II, 1990, # 2, p. 315 - 320
  作者：Mure, Minae、Nii, Kazumi、Inoue, Teruhisa、Itoh, Shinobu、Ohshiro, Yoshiki

  DOI：——

  日期：——
• Reaction of the trimethyl ester of coenzyme PQQ(PQQTME) and amines in organic media. Products and mechanism
  作者：Shinobu Itoh、Minae Mure、Masaki Ogino、Yoshiki Ohshiro

  DOI：10.1021/jo00024a030

  日期：1991.11

  The reaction of PQQTME (1, the trimethyl ester of coenzyme PQQ) and various amines in organic media was investigated in order to gain information on the chemistry of PQQ in vitro. The iminoquinone derivatives 2, 3, and 5 were isolated from the reaction of 1 with ammonia, tert-butylamine, and cyclopropylamine, respectively, in CH3CN. The reduction of 2 by methylhydrazine proceeded smoothly to give the aminophenol 2H2 in moderate yield. Detailed analysis of the products from the reaction of 1 (and its 1-methyl derivative 6) with n-propylamine, N-methylpropylamine, triethylamine, and several benzylamines established that the oxidation of amines by PQQTME proceeds via an ionic mechanism (addition-elimination and transamination) that involves a carbinolamine intermediate. PQQTME was also found to be an efficient turnover catalyst of the aerobic oxidation of benzylamines in CH3CN solution.