6-methyl[1,3]dioxolo[4,5-g]quinolin-8-amine | 1021439-82-6

• 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-methyl[1,3]dioxolo[4,5-g]quinolin-8-amine
• 英文别名: 6-Methyl-[1,3]dioxolo[4,5-g]quinolin-8-amine；6-methyl-[1,3]dioxolo[4,5-g]quinolin-8-amine
• CAS: 1021439-82-6
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: OVQMKARSSZEWBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methyl[1,3]dioxolo[4,5-g]quinolin-8-amine 、 p-isocyanophenyl mustard 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以58%的产率得到N-{4-[bis(2-chloroethyl)amino]phenyl}-N'-(6-methyl[1,3]dioxolo[4,5-g]quinolin-8-yl)urea
  参考文献：
  名称：

  Potent DNA-directed alkylating agents: Synthesis and biological activity of phenyl N-mustard–quinoline conjugates having a urea or hydrazinecarboxamide linker

  摘要：

  A series of N-mustard-quinoline conjugates bearing a urea or hydrazinecarboxamide linker was synthesized for antitumor evaluation. The in vitro cytotoxicity studies revealed that compounds with hydrazinecarboxamide linkers were generally more cytotoxic than the corresponding urea counterparts in inhibiting human lymphoblastic leukemia and various solid tumor cell growths in culture. The therapeutic efficacy against human tumor xenografts in animal model was studied. It was shown that complete tumor remission in nude mice bearing human breast carcinoma MX-1 xenograft by 17a, i and 18c, d was achieved. In the present study, it was revealed that both linkers are able to lower the chemically reactive N-mustard pharmacophore and thus the newly synthesized conjugates possess a long half-life in rat plasma. Moreover, the new N-mustard derivatives are able to induce DNA cross-linking either by modified comet assay or by alkaline agarose gel shift assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.061
• 作为产物：
  描述：

  6-metil-8-idrazino-1,3-diossol<4,5-g>chinolina 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到6-methyl[1,3]dioxolo[4,5-g]quinolin-8-amine
  参考文献：
  名称：

  微波辅助合成4-喹啉基肼，然后还原硼化镍：一种方便的制备4-氨基喹啉及其衍生物的方法

  摘要：

  氯化镍（II）/硼氢化钠组合用于将4-肼基喹啉衍生物还原为相应的苯胺。该还原方案被有效地应用于单取代肼的还原裂解。我们在本文中描述了4-肼基喹啉的微波辅助合成，其提供了高产率和快速的两步法，用于在温和条件下合成4-氨基喹啉作为抗疟原体。

  DOI：

  10.1016/j.tetlet.2008.01.128

文献信息

• Microwave-assisted synthesis of 4-quinolylhydrazines followed by nickel boride reduction: a convenient approach to 4-aminoquinolines and derivatives
  作者：Sandra Gemma、Gagan Kukreja、Pierangela Tripaldi、Maria Altarelli、Matteo Bernetti、Silvia Franceschini、Luisa Savini、Giuseppe Campiani、Caterina Fattorusso、Stefania Butini

  DOI：10.1016/j.tetlet.2008.01.128

  日期：2008.3

  Nickel(II) chloride/sodium borohydride combination was employed for the reduction of 4-hydrazinoquinoline derivatives to the corresponding anilines. This reductive protocol was efficiently applied for the reductive cleavage of monosubstituted hydrazines. We described herein the microwave-assisted synthesis of 4-hydrazinoquinolines, which furnished a high yielding and rapid two-step procedure for the

  氯化镍（II）/硼氢化钠组合用于将4-肼基喹啉衍生物还原为相应的苯胺。该还原方案被有效地应用于单取代肼的还原裂解。我们在本文中描述了4-肼基喹啉的微波辅助合成，其提供了高产率和快速的两步法，用于在温和条件下合成4-氨基喹啉作为抗疟原体。
• Quinolylhydrazones as novel inhibitors of Plasmodium falciparum serine protease PfSUB1
  作者：Sandra Gemma、Simone Giovani、Margherita Brindisi、Pierangela Tripaldi、Simone Brogi、Luisa Savini、Isabella Fiorini、Ettore Novellino、Stefania Butini、Giuseppe Campiani、Maria Penzo、Michael J. Blackman

  DOI：10.1016/j.bmcl.2012.06.023

  日期：2012.8

  Plasmodium falciparum subtilisin-like protease 1 (PfSUB1) is a serine protease that plays key roles in the egress of the parasite from red blood cells and in preparing the released merozoites for the subsequent invasion of new erythrocytes. The development of potent and selective PfSUB1 inhibitors could pave the way to the discovery of potential antimalarial drugs endowed with an innovative mode of action and consequently able to overcome the current problems of resistance to established chemotherapies. Through the screening of a proprietary library of compounds against PfSUB1, we identified hydrazone 2 as a hit compound. Here we report a preliminary investigation of the structure-activity relationships for a class of PfSUB1 inhibitors related to our identified hit. (C) 2012 Elsevier Ltd. All rights reserved.
• Potent DNA-directed alkylating agents: Synthesis and biological activity of phenyl N-mustard–quinoline conjugates having a urea or hydrazinecarboxamide linker
  作者：Rajesh Kakadiya、Huajin Dong、Amit Kumar、Dodia Narsinh、Xiuguo Zhang、Ting-Chao Chou、Te-Chang Lee、Anamik Shah、Tsann-Long Su

  DOI：10.1016/j.bmc.2010.01.061

  日期：2010.3

  A series of N-mustard-quinoline conjugates bearing a urea or hydrazinecarboxamide linker was synthesized for antitumor evaluation. The in vitro cytotoxicity studies revealed that compounds with hydrazinecarboxamide linkers were generally more cytotoxic than the corresponding urea counterparts in inhibiting human lymphoblastic leukemia and various solid tumor cell growths in culture. The therapeutic efficacy against human tumor xenografts in animal model was studied. It was shown that complete tumor remission in nude mice bearing human breast carcinoma MX-1 xenograft by 17a, i and 18c, d was achieved. In the present study, it was revealed that both linkers are able to lower the chemically reactive N-mustard pharmacophore and thus the newly synthesized conjugates possess a long half-life in rat plasma. Moreover, the new N-mustard derivatives are able to induce DNA cross-linking either by modified comet assay or by alkaline agarose gel shift assay. (C) 2010 Elsevier Ltd. All rights reserved.