9-(1H-1,2,3-苯并三唑-1-基)吖啶 | 741-71-9

• 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
• 中文名称: 9-(1H-1,2,3-苯并三唑-1-基)吖啶
• 英文名称: 9-(benzotriazol-1-yl)acridine
• CAS: 741-71-9
• 化学式: C₁₉H₁₂N₄
• 分子量: 296.331
• InChiKey: XMWYFZYDIFXQCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-(1H-1,2,3-苯并三唑-1-基)吖啶 在 盐酸 作用下， 生成 吖啶酮
  参考文献：
  名称：

  抗肿瘤多环a啶。第1部分。9-（1,2,3-三唑-1-基）ac啶的Graebe-Ullmann热解合成7H-吡啶基和8H-喹啉-[4,3,2-kl] r啶：差示扫描量热法的应用预测最佳环化条件

  摘要：

  差示扫描量热法研究了一系列在 9 位被 1,2,3-三唑-1-基、苯并三唑-1-基和萘并三唑-1-基取代的吖啶类化合物的热分解过程。单环三唑 7a 显示了一个离散的熔化端温度，随后是与 7H-吡啶并[4,3,2-kl]吖啶 8 的形成相对应的分解放热，而在苯并三唑 10aâe 和萘并三唑 10f 中，这些过程分别与环化成多环吖啶 11aâf 的单一急剧放热转变相吻合。利用沸腾的二苯醚作为分解介质，是以三唑前体为原料制备合成多环吖啶类化合物的最佳条件。在围位被甲基取代的苯并三唑-1-基吖啶 10e 表现异常：除了得到预期的 8H-喹啉并[4,3,2-kl]吖啶 11e 外，环化还导致甲基在自由基介导下脱落，形成未取代的 8H-喹啉并[4,3,2-kl]吖啶 11a，并从甲基析出 H，得到苯并氮杂环吖啶 12。9-(2-iodoanilino)acridine 16 的 Radical cyclisation 也得到了 8H-喹啉并[4,3,2-kl]吖啶 11a。11a 的晶体结构证实了分子间 N8âH Â- Â- Â- Â- N13 氢键的 8H 同分异构体排列，并显示出一个均方根偏差为 0.044 Ã 的平面多环体系。

  DOI：

  10.1039/a702299i
• 作为产物：
  描述：

  9-氯吖啶 在 盐酸 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 9-(1H-1,2,3-苯并三唑-1-基)吖啶
  参考文献：
  名称：

  The synthesis and evaluation of o-phenylenediamine derivatives as fluorescent probes for nitric oxide detection

  摘要：

  制备了一系列用于测定一氧化氮（NO）的分子探针。每个探针由与富电子邻苯二胺基团偶联的蒽、香豆素或吖啶荧光团组成。邻苯二胺基团可以被甲基或甲氧基取代以增强其富电子性质。通过从芳香胺到激发态荧光团的最低未占据轨道的光电子转移（PET），荧光团荧光被淬灭。与亚硝化物质的反应将邻苯二胺基团转化为缺电子苯并三唑衍生物。该基团具有较高的氧化电位，并且不会通过光电子转移猝灭荧光团的荧光，因此这些产品具有高荧光性。一些苯并三唑衍生物是通过替代合成路线制备的。通过用亚硝酸处理前体来评估荧光探针的形成 烟雾和 S-亚硝基-N-乙酰青霉胺 (SNAP)。

  DOI：

  10.1039/b105953j

文献信息

• Synthesis and properties of bioactive 2- and 3-amino-8-methyl-8H-quino[4,3,2-kl]acridine and 8,13-dimethyl-8H-quino[4,3,2-kl]acridinium saltsPart 15 in the series: Antitumour polycyclic acridines. See ref. 1. for part 14.
  作者：Ian Hutchinson、Andrew J. McCarroll、Robert A. Heald、Malcolm F. G. Stevens

  DOI：10.1039/b310796p

  日期：——

  Cyclisation of 9-(benzotriazol-1-yl)acridine 1 to the pentacycle 8H-quino[4,3,2-kl]acridine 5 in a range of low-boiling solvents is mechanistically distinct from previously published photochemical (carbene) and thermolytic (radical) cyclisations. Fragmentation of the triazole ring of 1 to a diazonium intermediate 7, and its subsequent heterolysis (–N2) and cyclisation is facilitated by solvation of intermediate zwitterionic species. Derivatives of 2- and 3-aminoquinoacridines methylated in the 8-position can be converted to 8,13-dimethylquino[4,3,2-kl]acridinium iodide salts with methyl iodide and were required for biological examination as potential telomerase inhibitors. The chloro group in 3-chloro-8-methyl-8H-quino[4,3,2-kl]acridine can be replaced efficiently by benzylamino, 4-morpholinyl and cyano substituents in palladium(0) mediated reactions.

  9-(1,2,3-苯并三氮唑-1-基)吖啶1在低沸点溶剂中环化生成五元环8H-喹喔啉[4,3,2-kl]吖啶5的机理与先前报道的光化学(碳烯)和热解(自由基)环化反应不同。1的苯并三氮唑环断裂生成中间体重氮盐7，随后发生异裂脱氮(-N2)和环化，这一过程得益于中间体两性离子的溶剂化作用。2-和3-氨基喹喔吖啶的甲基化衍生物在8-位甲基化后，可以通过甲基碘转化为8,13-二甲基喹喔啉[4,3,2-kl]吖啶碘盐，这些产物作为潜在的端粒酶抑制剂，需进行生物学检测。3-氯-8-甲基-8H-喹喔啉[4,3,2-kl]吖啶中的氯基可以高效地被苯甲氨基、4-吗啉基和氰基取代，这些反应都是通过钯(0)催化的反应完成的。
• Acridine and Quinoline Derivatives as Sirtuin Modulators
  申请人：Milburn Michael

  公开号：US20090069301A1

  公开（公告）日：2009-03-12

  Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, chemotherapeutic induced neuropathy, neuropathy associated with an ischemic event, polyglutamine diseases, ocular diseases and/or disorders, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本文提供了新颖的sirtuin调节化合物及其使用方法。这些sirtuin调节化合物可用于增加细胞寿命，并治疗和/或预防各种疾病和疾病，包括与衰老或压力有关的疾病或疾病，糖尿病，肥胖症，神经退行性疾病，化疗引起的神经病理性疼痛，缺血事件相关的神经病理性疼痛，多谷氨酸疾病，眼部疾病和/或疾病，心血管疾病，血栓形成障碍，炎症，癌症和/或潮红。还提供了包含sirtuin调节化合物与另一种治疗剂组合的组合物。
• Mitchell, Glynn; Rees, Charles W., Journal of the Chemical Society. Perkin transactions I, 1987, p. 403 - 412
  作者：Mitchell, Glynn、Rees, Charles W.

  DOI：——

  日期：——
• Antitumor Polycyclic Acridines. 7. Synthesis and Biological Properties of DNA Affinic Tetra- and Pentacyclic Acridines
  作者：Johnson Stanslas、Damien J. Hagan、Michael J. Ellis、Claire Turner、James Carmichael、Wynne Ward、Timothy R. Hammonds、Malcolm F. G. Stevens

  DOI：10.1021/jm9909490

  日期：2000.4.1

  New synthetic routes to a series of tetra- and pentacyclic acridines related in structure to marine natural products are reported. The novel water-soluble agent dihydroindolizino[7,6,5-kL]acridinium chloride 14 has inhibitory activity in a panel of non-small-cell lung and breast tumor cell lines exceeding that of m-AMSA. The salt inhibited the release of minicircle products of kDNA confirming that disorganization of topoisomerase II partly underlies the activity of the compound. COMPARE analysis of the NCI mean graph profile of compound 14 at the GI(50) level corroborates this conclusion with Pearson correlation coefficients (>0.6) to clinical agents of the topoisomerase II class: however, this correlation was not seen at the LC50 level. The inhibitory action of 14 on Saccharomyces cerevisiae transfected with human topoisomerase II isoforms showed a 3-fold selectivity against the II alpha isoform over the II beta isoform. Unlike nt-AMSA, 14 is not susceptible to P-glycoprotein-mediated drug efflux and retains activity in lung cells with derived resistance to the topoisomerase II inhibitor etoposide.
• Antitumor Polycyclic Acridines. 8. Synthesis and Telomerase-Inhibitory Activity of Methylated Pentacyclic Acridinium Salts
  作者：Robert A. Heald、Chetna Modi、Jenny C. Cookson、Ian Hutchinson、Charles A. Laughton、Sharon M. Gowan、Lloyd R. Kelland、Malcolm F. G. Stevens

  DOI：10.1021/jm011015q

  日期：2002.1.1

  Two short routes to novel methylated pentacyclic quinoacridinium salts have been devised. New compounds display telomerase-inhibitory potency (<1 muM) in the TRAP assay. 3,11-Difluoro-6,8,13-trimethyl-8H-quino[4,3,2-kl]acridinium methosulfate (12d, RHPS4, NSC 714187) has a higher selectivity for triplex and quadruplex DNA structures than the 3,6,8,11,13-pentamethyl analogue (12c, RHPS3, NSC 714186) and a low overall growth-inhibitory activity in the NCI 60 cell panel (mean GI(50) 13.18 muM); in addition, the activity profile of 12d does not COMPARE with agents of the topoisomerase II class. Compound 12d is soluble in water, stable in the pH range of 5-9, efficiently transported into tumor cells, and is currently the lead structure for further elaboration in this new class of telomerase inhibitor.