3-amino-7-methoxy-1H-pyrazolo[3,4-b]quinoline | 129797-61-1

• 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
• 英文名称: 3-amino-7-methoxy-1H-pyrazolo[3,4-b]quinoline
• 英文别名: 7-methoxy-1H-pyrazolo[3,4-b]quinolin-3-amine；7-methoxy-1H-pyrazolo[3,4-b]quinolin-3-ylamine；7-methoxy-2H-pyrazolo[3,4-b]quinolin-3-amine
• CAS: 129797-61-1
• 化学式: C₁₁H₁₀N₄O
• mdl: MFCD00895692
• 分子量: 214.227
• InChiKey: QLIPUPSGLWIGAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  276 °C(Solv: water (7732-18-5))
• 沸点：
  518.7±45.0 °C(Predicted)
• 密度：
  1.440±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  76.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-7-methoxy-1H-pyrazolo[3,4-b]quinoline 在 ammonium hydroxide 、 sodium dithionite 、 sodium ethanolate 、 sodium acetate 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 7.5h， 生成 9-methoxy-3-acetylamino-4-aminoquinolino[2',3'-5,4](3-1H-pyrazolino)[2,3-a]pyrimidin-2-one
  参考文献：
  名称：

  Synthesis and Benzodiazepine Receptor Binding Activity of 2, 9-Disubstituted Quinolino[2′, 3′-5, 4](3-pyrazolino)[3, 2-b]purin-4-ones

  摘要：

  2,9-Disubstituted quinolino[2',3'-5,4](3-pyrazolino)pyrimidin-2-ones and purin-4-ones were synthesized and their benzodiazepine receptor activity was evaluated for their ability to displace [H-3]R015-1788 from its specific binding in bovine brain membranes. Compound 5c caused 83+/-8% inhibition in [3H]R015-1788 specific benzodiazepine receptor binding followed by compounds 5f, 5h, and 5i while other analogs were inactive at 10 muM concentration.

  DOI：

  10.1002/1521-4184(200205)335:5<207::aid-ardp207>3.0.co;2-5
• 作为产物：
  描述：

  2-氯-7-甲氧基喹啉-3-甲醛 在 ammonium hydroxide 、 hydrazine hydrate 、 盐酸羟胺 作用下， 生成 3-amino-7-methoxy-1H-pyrazolo[3,4-b]quinoline
  参考文献：
  名称：

  升ħ -吡唑并[3,4- b ]喹啉-3-胺衍生物抑制结肠癌细胞的生长通过凋亡和亚G1细胞周期停滞

  摘要：

  合成了一系列1 H-吡唑并[3,4- b ]喹啉-3-胺衍生物，并评估了十种癌细胞系（包括乳腺癌（MDAMB-231和MCF-7），结肠（ HCT-116，HCT-15，HT-29和LOVO），前列腺（DU-145和PC3），脑（LN-229），卵巢（A2780）和人胚肾（HEK293）细胞（非癌细胞）线。在筛选的八种衍生物中，化合物QTZ05在四种结肠癌细胞系中具有最强效和选择性的抗肿瘤功效，IC 50值范围为2.3至10.2 µM。此外，QTZ05以浓度依赖的方式抑制HCT-116细胞中的集落形成。细胞周期分析数据表明，QTZ05导致HCT-116细胞亚G1细胞周期停滞。QTZ05以浓度依赖的方式诱导HCT-116细胞凋亡，其特征在于染色质浓缩和荧光素偶联膜联蛋白V的荧光增强。我们的研究结果表明QTZ05可能是化学疗法发展的有价值的原型靶向大肠癌细胞的凋亡途径。

  DOI：

  10.1016/j.bmcl.2018.05.045

文献信息

• Pyrazolo[3,4-b]quinolines and their use as antiviral agents
  申请人：Sterling Drug Inc.

  公开号：US04920128A1

  公开（公告）日：1990-04-24

  Pyrazolo[3,4-b]quinolines having the formula ##STR1## where R is hydrogen, hydroxy or alkoxy; R.sub.2 is halogen, cyano, carbamyl, carboxy, lower-alkylcarbonyl, amino or aminomethyl; and R.sub.1 is hydrogen or selected substituents as defined herein, are useful as antiviral agents and/or as vasodilators.

  具有以下化学式的吡唑[3,4-b]喹啉化合物：##STR1## 其中R为氢、羟基或烷氧基；R.sub.2为卤素、氰基、氨基甲酰基、羧基、较低烷基羰基、氨基或氨甲基；R.sub.1为氢或根据本文定义的选择性取代基，可用作抗病毒剂和/或血管扩张剂。
• Evaluation of Some Pyrazoloquinolines as Inhibitors of Herpes Simplex Virus Type 1 Replication
  作者：Adnan A. Bekhit、Ola A. El-Sayed、Hassan Y. Aboul-Enein、Yunus M. Siddiqui、Mohammed N. Al-Ahdal

  DOI：10.1002/ardp.200400930

  日期：2005.3

  Three structurally related aminopyrazoloquinoline derivatives were evaluated for their antiviral activity against Herpes Simplex virus type 1. These compounds were examined for their in vitro antiviral activity by two different bioassays, namely; crystal violet staining and tetrazolium dye (MTS) measurement. The antiviral role of these compounds was confirmed by enumerating the infectious particles

  评估了三种结构相关的氨基吡唑并喹啉衍生物对 1 型单纯疱疹病毒的抗病毒活性。通过两种不同的生物测定法检查了这些化合物的体外抗病毒活性，即；结晶紫染色和四唑鎓染料 (MTS) 测量。这些化合物的抗病毒作用通过用斑块测定计数感染性颗粒得到证实。生物活性化合物的急性毒性值是在筛选为抗病毒剂之前确定的。
• Srivastava, Ambika; Singh, Mrityunjay K.; Singh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 1, p. 292 - 296
  作者：Srivastava, Ambika、Singh, Mrityunjay K.、Singh

  DOI：——

  日期：——
• Regioselective acylation of congeners of 3-amino-1H-pyrazolo[3,4-b]quinolines, their activity on bacterial serine/threonine protein kinases and in vitro antibacterial (including antimycobacterial) activity
  作者：Gennady B. Lapa、O. B. Bekker、E. P. Mirchink、V. N. Danilenko、M. N. Preobrazhenskaya

  DOI：10.3109/14756366.2012.716056

  日期：2013.10.1

  It was found by virtual screening that 3-amino-1H-pyrazolo[3,4-b]quinolines could have wide protein kinase inhibitory activity. Amides of titled amines and thioureas were synthesized regioselectively. 3-Amino-7-methoxy-1Hpyrazolo[3,4-b]quinoline demonstrated in vitro significant inhibitory activity on bacterial serine/threonine protein kinases (inhibition of resistance to kanamycin in Streptomyces lividans regulated by protein kinases). The studies of Structure Activity Relationship (SAR) showed that the substitution of the NH2 group and 1-NH of pyrazole ring or aromatic ring at the position 6 decreased or removed inhibitory activity.
• BELL, MALCOLM R.;ACKERMAN, JAMES H.
  作者：BELL, MALCOLM R.、ACKERMAN, JAMES H.

  DOI：——

  日期：——