4-(3,3,6,6-tetramethyl-9-(4-nitrophenyl)-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)benzenesulfonamide | 1426925-49-6

• 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: 4-(3,3,6,6-tetramethyl-9-(4-nitrophenyl)-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)benzenesulfonamide
• 英文别名: 4-[3,3,6,6-tetramethyl-9-(4-nitrophenyl)-1,8-dioxo-4,5,7,9-tetrahydro-2H-acridin-10-yl]benzenesulfonamide
• CAS: 1426925-49-6
• 化学式: C₂₉H₃₁N₃O₆S
• 分子量: 549.648
• InChiKey: XELJYZITRZHXDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  39
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(3,3,6,6-tetramethyl-9-(4-nitrophenyl)-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)benzenesulfonamide 在 sodiumsulfide nonahydrate 、 sulfur 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成 4-bromo-N-(4-(3,3,6,6-tetramethyl-1,8-dioxo-10-(4-sulfamoylphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridin-9-yl)phenyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis of novel acridine bis-sulfonamides with effective inhibitory activity against the carbonic anhydrase isoforms I, II, IX and XII

  摘要：

  By using a multi component reaction system (MCR), nitro acridine sulfonamides were obtained from cyclic-1,3-diketones, 4-aminobenzene sulfonamide and aromatic aldehydes. Some novel acridine bis-sulfonamides 6a-l were then synthesized by the reaction between sulfonyl chlorides and the novel amino-acridine sulfonamides 5a and 5b, obtained by reduction of nitro-acridine sulfonamide derivatives 4a and 4b. The newly synthesized compounds were investigated as inhibitors of 4 human carbonic anhydrase isoforms (hCA, EC 4.2.1.1). Several of the compounds showed low micromolar inhibition against the medically relevant isoforms hCA I, II, IX, and XII. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.022
• 作为产物：
  描述：

  对硝基苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 磺胺 在 碘 作用下， 以 异丙醇 为溶剂， 反应 0.17h， 以96%的产率得到4-(3,3,6,6-tetramethyl-9-(4-nitrophenyl)-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)benzenesulfonamide
  参考文献：
  名称：

  Iodine-catalyzed three-component one-pot synthesis of novel 1,8-dioxo-decahydroacridines derivatives bearing benzene sulfonamide moiety

  摘要：

  本研究描述了一种具有生物活性磺酰胺分子的 1,8-二氧代十氢吖啶衍生物的高效合成方法。在分子碘作为催化剂的作用下，芳香醛与 5,5-二甲基-1,3-环己二酮和磺胺发生反应，得到 1,8-二氧代十氢吖啶衍生物，收率高至极佳。这些化合物的结构是根据元素分析（C、H 和 N）和光谱分析（1H NMR、13C NMR、MS 和 FTIR）确定的。通过 3-(4,5-二甲基噻唑-2-基)-2,5-二苯基溴化四氮唑（MTT）测定法，对所有化合物对三种人类肿瘤细胞系（人类乳腺癌细胞（MCF-7）、人类宫颈癌细胞（Hela）和人类肺癌细胞（A549）的细胞毒活性进行了体外测试。大多数化合物对受试细胞株都显示出中等至强效的细胞毒性活性。其中，活性最强的化合物 4e 对 MCF-7 细胞的活性（10.92 μM）高于顺铂（11.06 μM）。

  DOI：

  10.1007/s11164-013-1105-4

文献信息

• One-pot synthesis of symmetrical and unsymmetrical acridine sulfonamide derivatives catalyzed by p-TSA
  作者：Cinnathambi Subramani Maheswari、Rathinam Ramesh、Appaswami Lalitha

  DOI：10.1007/s11164-017-2870-2

  日期：2017.7

  Abstract Synthesis of a series of symmetrical and unsymmetrical 1,8-dioxo-octahydroacridine benzenesulfonamide derivatives has been achieved by one-pot, multicomponent reaction of aromatic aldehydes and sulfanilamide with cyclic 1,3-dicarbonyl compounds by using p -toluenesulfonic acid as an effective, cheap, and efficient catalyst. Reaction progress was monitored by thin-layer chromatography (TLC)

  摘要 以 对 甲苯磺酸为有效成分，通过芳族醛和磺胺与环1,3-二羰基化合物的一锅多反应，合成了一系列对称且不对称的1,8-二氧-八氢ac啶苯磺酰胺衍生物。 ，便宜，高效的催化剂。通过薄层色谱（TLC）监测反应进程，并通过傅立叶变换红外光谱（FT-IR），1 H和13 C核磁共振（NMR）和质谱（MS）分析产物。 图形概要
• Synthesis of novel acridine bis-sulfonamides with effective inhibitory activity against the carbonic anhydrase isoforms I, II, IX and XII
  作者：İbrahim Esirden、Ramazan Ulus、Burak Aday、Muhammet Tanç、Claudiu T. Supuran、Muharrem Kaya

  DOI：10.1016/j.bmc.2015.09.022

  日期：2015.10

  By using a multi component reaction system (MCR), nitro acridine sulfonamides were obtained from cyclic-1,3-diketones, 4-aminobenzene sulfonamide and aromatic aldehydes. Some novel acridine bis-sulfonamides 6a-l were then synthesized by the reaction between sulfonyl chlorides and the novel amino-acridine sulfonamides 5a and 5b, obtained by reduction of nitro-acridine sulfonamide derivatives 4a and 4b. The newly synthesized compounds were investigated as inhibitors of 4 human carbonic anhydrase isoforms (hCA, EC 4.2.1.1). Several of the compounds showed low micromolar inhibition against the medically relevant isoforms hCA I, II, IX, and XII. (c) 2015 Elsevier Ltd. All rights reserved.
• Iodine-catalyzed three-component one-pot synthesis of novel 1,8-dioxo-decahydroacridines derivatives bearing benzene sulfonamide moiety
  作者：Shenghui Li、Shan Ding、Shengjie Xu、Jinchao Zhang、Shuxiang Wang、Chuanqi Zhou、Xiaoliu Li

  DOI：10.1007/s11164-013-1105-4

  日期：2014.5

  An efficient synthetic method for 1,8-dioxo-decahydroacridines derivatives bearing the biologically active sulfonamide moiety is described. Aromatic aldehyde reacted with 5,5-dimethyl-1,3-cyclohexanedione and sulfanilamide, with molecular iodine as catalyst, to give 1,8-dioxo-decahydroacridines derivatives in high to excellent yield. The structures of these compounds were established on the basis of elemental (C, H and N) and spectral analysis (1H NMR, 13C NMR, MS and FTIR). All the compounds were tested for their cytotoxic activity in vitro against three human tumor cell lines: human mammary cancer cells (MCF-7), human cervical carcinoma cells (Hela), and human lung cancer cells (A549) by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Most of them showed moderate to potent cytotoxic activity against the tested cell lines. Among them, the most active compound 4e exhibited more efficient activity (10.92 μM) against MCF-7 cells than cisplatin (11.06 μM).

  本研究描述了一种具有生物活性磺酰胺分子的 1,8-二氧代十氢吖啶衍生物的高效合成方法。在分子碘作为催化剂的作用下，芳香醛与 5,5-二甲基-1,3-环己二酮和磺胺发生反应，得到 1,8-二氧代十氢吖啶衍生物，收率高至极佳。这些化合物的结构是根据元素分析（C、H 和 N）和光谱分析（1H NMR、13C NMR、MS 和 FTIR）确定的。通过 3-(4,5-二甲基噻唑-2-基)-2,5-二苯基溴化四氮唑（MTT）测定法，对所有化合物对三种人类肿瘤细胞系（人类乳腺癌细胞（MCF-7）、人类宫颈癌细胞（Hela）和人类肺癌细胞（A549）的细胞毒活性进行了体外测试。大多数化合物对受试细胞株都显示出中等至强效的细胞毒性活性。其中，活性最强的化合物 4e 对 MCF-7 细胞的活性（10.92 μM）高于顺铂（11.06 μM）。