1-phenyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole | 17071-83-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-phenyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 英文别名: 2-Tosyl-1-phenyl-1,2,3,4-tetrahydro-β-carbolin；2-(4-Methylphenyl)sulfonyl-1-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indole
• CAS: 17071-83-9
• 化学式: C₂₄H₂₂N₂O₂S
• 分子量: 402.517
• InChiKey: VKJDUXNXSMIHEF-UHFFFAOYSA-N

物化性质

• 沸点：
  613.1±65.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 以95%的产率得到1-phenyl-4,9-dihydro-3H-β-carboline
  参考文献：
  名称：

  Mild and Efficient Syntheses of 1-Aryl-3,4-dihydroisoquinolines and 1-Aryl-3,4-dihydro-β-carbolines via Regiospecific β-Eliminations of the CorrespondingN-Tosyl-1,2,3,4-tetrahydroisoquinolines andN-Tosyl-1,2,3,4-tetrahydro-β-carbolines

  摘要：

  Treatment of N-tosyl-1-aryl-1,2,3,4-tetrahydro-isoquinolines or N-tosyl-1-aryl-1, 2,3,4-tetrahydro-beta-carbolines with a strong base such as NaOH or KOH at 70 degrees C in dimethylsulfoxide (DMSO) produced 1-aryl-3,4-dihydroisoquinolines or 1-aryl-3,4-dihydro-beta-carbolines in good yields via mild and regiospecific beta-eliminations. A dramatic solvent effect was observed, DMSO was crucial for the reactions. The temperature is also crucial for the reactions and should be kept between 60 and 80 degrees C.

  DOI：

  10.1080/00397911.2011.568659
• 作为产物：
  描述：

  N-tosyl tryptamine 在 四氯化锡 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.2h， 生成 1-phenyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  1-Substituted β-Carbolines by a Pictet−Spengler Cyclization with Thioortho Esters and Carbon−Carbon Bond Formation via N-Sulfonyl Iminium Ions Generated from N,S-Sulfonyl Acetals

  摘要：

  [GRAPHICS]The reaction of N-tosyltryptamines with thioortho esters, leading to 1-thiosubstituted tetrahydro-beta-carbolines under modified Pictet-Spengler conditions, is described. The 1-heterosubstituted beta-carbolines furnished 1-substituted beta-carbolines upon reaction with Grignard reagents and silyl derivatives under Lewis acid promotion.

  DOI：

  10.1021/ol051342i

文献信息

• 一种环金属化β-咔啉类钌配合物及其制备方法和应用
  申请人：广东医科大学

  公开号：CN106632490A

  公开（公告）日：2017-05-10

  本发明涉及抗肿瘤药物技术领域，具体公开了一种环金属化β‑咔啉类钌配合物及其制备方法和应用。所述的钌配合物以1‑phenyl‑9H‑pyrido[3,4‑b]indole为主配体，以2,2‑联吡啶或4,4‑二甲基‑2,2联吡啶为辅助配体。该钌配合物具有非常优异的抗肿瘤作用；尤其对肝癌、乳腺癌、肺癌及宫颈癌细胞株表现出比顺铂及类似的多吡啶咔啉类钌配合物更优越的活性。
• Efficient and Practical One-Pot Conversions of N-Tosyltetrahydroisoquinolines into Isoquinolines and of N-Tosyltetrahydro-β-carbolines into β-Carbolines through Tandem β-Elimination and Aromatization
  作者：Jing Dong、Xiao-Xin Shi、Jing-Jing Yan、Jing Xing、Qiang Zhang、Sen Xiao

  DOI：10.1002/ejoc.201001153

  日期：2010.12

  An efficient, practical, and general method for conversions of N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) into isoquinolines and of N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) into β-carbolines is described. Treatment of N-tosyl-THIQs or N-tosyl-THBCs with base in dimethyl sulfoxide afforded dihydroisoquinolines or dihydro-β-carbolines as intermediates, and these were then oxidized in situ by

  描述了一种将 N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) 转化为异喹啉和将 N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) 转化为 β-咔啉的有效、实用和通用的方法。在二甲基亚砜中用碱处理 N-tosyl-THIQs 或 N-tosyl-THBCs 得到作为中间体的二氢异喹啉或二氢-β-咔啉，然后这些被分子氧原位氧化得到异喹啉或 β-咔啉。产量。两种一锅法转化都是通过串联β-消除和芳构化发生的。
• Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer
  作者：Yuan-Qiong Huang、Hong-Jian Song、Yu-Xiu Liu、Qing-Min Wang

  DOI：10.1002/chem.201705202

  日期：2018.2.9

  some of the methods are hampered by long reaction times, harsh conditions, and the need for catalysts that are not readily available. This work reports a novel method for dehydrogenation of N‐heterocycles. Specifically, O2.− generated in situ acts as the oxidant for N‐heterocycle substrates that are susceptible to oxidation through a hydrogen atom transfer mechanism. This method provides a general

  在许多药物，天然产物和合成材料中都发现了含氮杂芳烃基序。尽管已经报道了几种通过相应的饱和杂环的脱氢合成这些化合物的优美方法，但是其中一些方法因反应时间长，苛刻的条件以及对催化剂的需求而难以获得。这项工作报告了一种新的N-杂环脱氢方法。具体而言，原位生成的O 2 .-充当N杂环底物的氧化剂，这些底物易受氢原子转移机制的氧化。这种方法为通向N-杂芳烃提供了一条通用的绿色路线。
• TCCA-mediated oxidative rearrangement of tetrahydro-β-carbolines: facile access to spirooxindoles and the total synthesis of (±)-coerulescine and (±)-horsfiline
  作者：Manda Sathish、Akash P. Sakla、Fabiane M. Nachtigall、Leonardo S. Santos、Nagula Shankaraiah

  DOI：10.1039/d1ra02381k

  日期：——

  Multi-reactive centered reagents are beneficial in chemical synthesis due to their advantage of minimal material utilization and formation of less by-products. Trichloroisocyanuric acid (TCCA), a reagent with three reactive centers, was employed in the synthesis of spirooxindoles through the oxidative rearrangement of various N-protected tetrahydro-β-carbolines. In this protocol, low equivalents of

  多反应中心试剂由于其材料利用率最低和副产物形成较少的优点而在化学合成中是有益的。三氯异氰尿酸 (TCCA) 是一种具有三个反应中心的试剂，可通过各种N保护的四氢-β-咔啉的氧化重排来合成螺氧吲哚。在该协议中，需要低当量的 TCCA 才能获得具有广泛底物范围的螺氧吲哚（高达 99% 的产率）。此外，该协议的适用性和稳健性已被证明可用于以优异的产量合成 (±)-coerulescine ( 1 ) 和 (±)-horsfiline ( 2 )等天然生物碱的克级全合成。
• Synthesis, characterization, cellular uptake and apoptosis-inducing properties of two highly cytotoxic cyclometalated ruthenium(II) β-carboline complexes
  作者：Jincan Chen、Fa Peng、Yao Zhang、Baojun Li、Ji She、Xinming Jie、Zhilin Zou、Man Chen、Lanmei Chen

  DOI：10.1016/j.ejmech.2017.09.007

  日期：2017.11

  (1-phenyl-9H-pyrido[3,4-b]indole) is a β-carboline alkaloids derivatives, have been synthesized and characterized. The in vitro cytotoxicities, cellular uptake and localization, cell cycle arrest and apoptosis-inducing mechanisms of these complexes have been extensively explored by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, inductively coupled plasma mass spectrometry (ICP-MS)

  两种新的通式为[Ru（NN）2（1-Ph-βC）]（PF 6）的环金属化Ru（II）络合物，其中N–N = 4,4'-二甲基-2,2'-联吡啶（ dmb，Ru1），2,2'-联吡啶（bpy，Ru2）和1-Ph-βC（1-苯基-9 H-吡啶[3,4- b[吲哚]是β-咔啉生物碱的衍生物，已经合成并表征。这些配合物的体外细胞毒性，细胞摄取和定位，细胞周期阻滞和凋亡诱导机制已通过3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物（MTT）测定法进行了广泛探索。 ，电感耦合等离子体质谱（ICP-MS），流式细胞仪，彗星分析，倒置荧光显微镜以及蛋白质印迹实验技术。值得注意的是，Ru1和Ru2对具有IC 50的选定人类癌细胞系表现出有效的抗增殖活性的值低于顺铂和其他非环金属化的Ru（II）β-咔啉配合物的值。细胞摄取和定位表明这些复合物可以在细胞核中积累。进一步的抗肿瘤机制研究表明，Ru1和