10-(4-chlorobutyl) acridone | 692776-72-0

• 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: 10-(4-chlorobutyl) acridone
• 英文别名: 10-(4-Chlorobutyl)acridin-9-one
• CAS: 692776-72-0
• 化学式: C₁₇H₁₆ClNO
• 分子量: 285.773
• InChiKey: SIERXYVLONSSPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-羟乙基哌嗪 、 10-(4-chlorobutyl) acridone 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 以54%的产率得到10-[4-[4-(2-Hydroxyethyl)piperazin-1-yl]butyl]acridin-9-one
  参考文献：
  名称：

  Anti-calmodulin acridone derivatives modulate vinblastine resistance in multidrug resistant (MDR) cancer cells

  摘要：

  Multidrug resistance (MDR) is one of the main obstacles limiting the efficacy of chemotherapy treatment of tumors. Parent acridones 1A and 1B were prepared by the Ullmann reaction followed by cyclization and N-alkylation. N-(omega-Chloroalkyl) analogues were subjected to iodide catalyzed nucleophilic Substitution reaction with secondary amines to get the compounds 3A-13A and 3B-13B, which enhanced the uptake of vinblastine in KBCh(R)-8-5 cells to a greater extent (2.6-13.1-fold relative to control) than verapamil. The study oil the structure-activity relationship revealed that substitution of -H at position C-4 in acridone nucleus by -OCH3 increased the cytotoxic and anti-MDR activities. The ability of acridones to inhibit calmodulin dependent cyclic AMP phosphodiesterase has been determined and the results have shown a strong positive correlation between anti-calmodulin activity and cytotoxicity in KBCh(R)-8-5 cells or anti-MDR activity. (C) 2003 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.12.001
• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 氢氧化钾 、 PPA 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 10-(4-chlorobutyl) acridone
  参考文献：
  名称：

  Anti-calmodulin acridone derivatives modulate vinblastine resistance in multidrug resistant (MDR) cancer cells

  摘要：

  Multidrug resistance (MDR) is one of the main obstacles limiting the efficacy of chemotherapy treatment of tumors. Parent acridones 1A and 1B were prepared by the Ullmann reaction followed by cyclization and N-alkylation. N-(omega-Chloroalkyl) analogues were subjected to iodide catalyzed nucleophilic Substitution reaction with secondary amines to get the compounds 3A-13A and 3B-13B, which enhanced the uptake of vinblastine in KBCh(R)-8-5 cells to a greater extent (2.6-13.1-fold relative to control) than verapamil. The study oil the structure-activity relationship revealed that substitution of -H at position C-4 in acridone nucleus by -OCH3 increased the cytotoxic and anti-MDR activities. The ability of acridones to inhibit calmodulin dependent cyclic AMP phosphodiesterase has been determined and the results have shown a strong positive correlation between anti-calmodulin activity and cytotoxicity in KBCh(R)-8-5 cells or anti-MDR activity. (C) 2003 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.12.001

文献信息

• Design, Synthesis, and Evaluation of 10-N-Substituted Acridones as Novel Chemosensitizers in <i>Plasmodium falciparum</i>
  作者：Jane X. Kelly、Martin J. Smilkstein、Roland A. Cooper、Kristin D. Lane、Robert A. Johnson、Aaron Janowsky、Rozalia A. Dodean、David J. Hinrichs、Rolf Winter、Michael Riscoe

  DOI：10.1128/aac.00669-07

  日期：2007.11

  synthesized, and evaluated for the ability to enhance the potency of quinoline drugs against multidrug-resistant (MDR) Plasmodium falciparum malaria parasites. A number of acridone derivatives, with side chains bridged three or more carbon atoms apart between the ring nitrogen and terminal nitrogen, demonstrated chloroquine (CQ)-chemosensitizing activity against the MDR strain of P. falciparum (Dd2). Isobologram

  设计，合成并评估了一系列新颖的10-N-取代的cri烯，它们在末端带有叔胺基的烷基侧链，并评估了增强喹啉类药物对抗多药耐药性（MDR）恶性疟原虫的效力的能力。疟原虫。许多a啶酮衍生物的侧链在环氮和末端氮之间桥接三个或三个以上的碳原子，它们显示出对恶性疟原虫（Dd2）MDR菌株的氯喹（CQ）化学增敏活性。等效线分析法显示，选定的候选物在耐CQ（CQR）的寄生虫Dd2中表现出与CQ显着的协同作用，但在CQ敏感（CQS）D6中仅发生加性（或无关紧要）相互作用。这些a啶酮衍生物还增强了其他喹啉类抗疟药的敏感性，例如Dd2中的去乙基氯喹（DCQ）和奎宁（QN）。选定的cri啶酮对CQ和QN的化学增敏作用模式类似于维拉帕米针对各种寄生虫株的化学增敏作用，其突变编码恶性疟原虫CQ抗性转运蛋白（PfCRT）的氨基酸76。与其他已知的具有公认的精神治疗作用的化学增敏剂（例如地昔帕明，丙咪嗪和氯苯那敏）不同，
• 一种光催化环己烯水合反应制备环己醇的方法
  申请人：浙江大学

  公开号：CN117756603A

  公开（公告）日：2024-03-26

  本发明公开了一种光催化环己烯水合反应制备环己醇的方法：惰性气体保护下，式II所示的环己烯和水，在有机溶剂中，在光催化剂、助催化剂的催化作用下，在光源照射下进行水合反应，制得式I所示的环己醇；所述光催化剂为式III所示的吖啶盐类化合物。本发明方法原子经济性高，无副产物产生，对环境友好，有广泛的工业应用前景。本发明的光催化水合反应制备环己醇的单程收率可达30％以上，相比现有技术收率显著提高。#imgabs0#
• Anti-calmodulin acridone derivatives modulate vinblastine resistance in multidrug resistant (MDR) cancer cells
  作者：Ravi Hegde、Padma Thimmaiah、Mayur C Yerigeri、Gowdahalli Krishnegowda、Kuntebommanahalli N Thimmaiah、Peter J Houghton

  DOI：10.1016/j.ejmech.2003.12.001

  日期：2004.2

  Multidrug resistance (MDR) is one of the main obstacles limiting the efficacy of chemotherapy treatment of tumors. Parent acridones 1A and 1B were prepared by the Ullmann reaction followed by cyclization and N-alkylation. N-(omega-Chloroalkyl) analogues were subjected to iodide catalyzed nucleophilic Substitution reaction with secondary amines to get the compounds 3A-13A and 3B-13B, which enhanced the uptake of vinblastine in KBCh(R)-8-5 cells to a greater extent (2.6-13.1-fold relative to control) than verapamil. The study oil the structure-activity relationship revealed that substitution of -H at position C-4 in acridone nucleus by -OCH3 increased the cytotoxic and anti-MDR activities. The ability of acridones to inhibit calmodulin dependent cyclic AMP phosphodiesterase has been determined and the results have shown a strong positive correlation between anti-calmodulin activity and cytotoxicity in KBCh(R)-8-5 cells or anti-MDR activity. (C) 2003 Elsevier SAS. All rights reserved.