4-(9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)benzenesulfonamide | 1392416-98-6

• 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-(9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)benzenesulfonamide
• 英文别名: 4-(9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridine-10(9H)-yl)benzenesulfonamide；4-(9-(4-Methoxyphenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydro acridine-10(9H)-yl)benzenesulfonamide (5)；4-[9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-1,8-dioxo-4,5,7,9-tetrahydro-2H-acridin-10-yl]benzenesulfonamide
• CAS: 1392416-98-6
• 化学式: C₃₀H₃₄N₂O₅S
• 分子量: 534.676
• InChiKey: GUCLVCBTPLFYKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 磺胺 在 choline chloride-urea 作用下， 反应 0.5h， 以93%的产率得到4-(9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)benzenesulfonamide
  参考文献：
  名称：

  快速和绿色的方法方便地多组分合成N-取代的十氢ac啶-1,8-二酮作为潜在的抗菌剂

  摘要：

  摘要 通过各种芳香醛（ 1a – q ），二甲基二酮（ 2 ）和各种芳香胺的多组分反应，获得了一种高效，绿色，高产且快速的合成N-取代十氢ac啶-1,8-二酮的方法。 （ 2a – d ）使用ChCl：尿素深共晶溶剂作为可回收的有机催化剂和介质。反应条件相对温和，不需要其他金属，酸催化剂或有机溶剂。温和的反应条件，简单的实验，简单的纯化程序，短的反应时间即可获得出色的收率，以及绿色化学原理的应用，都是这种方法的优势。这种易于从氯化胆碱和尿素合成的简单的铵深共晶溶剂相对便宜且可生物降解，使其可用于工业用途。深共晶溶剂易于分离和重复使用而不会失去活性，因此提供了一个很好的选择。合成的10-（取代的苯基）-9-（取代的苯基）-3,3,6,6-四甲基-3,4,6,7,9,10-六氢ac啶-1， 筛选了 4a - l ）对四种细菌革兰氏阳性菌（ 金黄色葡萄球菌 和 枯草芽孢杆菌 ），革兰氏阴性菌（ 大肠杆菌

  DOI：

  10.1007/s11164-018-3541-7

文献信息

• 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）。
• 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 and characterization of novel dioxoacridine sulfonamide derivatives as new carbonic anhydrase inhibitors
  作者：Muharrem Kaya、Erhan Basar、Emrah Çakir、Ekrem Tunca、Metin Bülbül

  DOI：10.3109/14756366.2011.599029

  日期：2012.8.1

  Novel dioxoacridine sulfonamide compounds were synthesized from reaction of cyclic 1,3-diketones, sulfanilamide (4-amino benzene sulfonamide) and aromatic aldehydes. The structures of these compounds were confirmed by using spectral analysis (IR, H-NMR, C-13-NMR, and mass). Human carbonic anhydrase isoenzymes (hCA I and hCA II) were purified from erythrocyte cells by affinity chromatography. The inhibitory effects of sulfanilamide, acetazolamide (AAZ), and newly synthesized sulfonamides on hydratase and esterase activities of these isoenzymes have been studied in vitro. The IC50 values of compounds for esterase activity are 0.71-0.11 mu M for hCA I and 0.45-0.12 mu M for hCA II, respectively. The K-i values of these inhibitors were determined as 0,38-0,008 mu M for hCA I and 0,19-0,001 mu M for hCA II, respectively.