1-(3,4-dimethoxyphenyl)-β-carboline | 94258-44-3

• 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-(3,4-dimethoxyphenyl)-β-carboline
• 英文别名: 1-(3,4-dimethoxyphenyl)-9H-pyrido[3,4-b]indole
• CAS: 94258-44-3
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: OYZZXAYYRMPAJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 1-(3,4-dimethoxyphenyl)-β-carboline 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 sodium acetate 、 zinc dibromide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以75%的产率得到(2,3-dimethoxy-6-(9H-pyrido[3,4-b]indol-1-yl)phenyl)methanol
  参考文献：
  名称：

  Ru(II)-Catalyzed Regioselective Hydroxymethylation of β-Carbolines and Isoquinolines via C–H Functionalization: Probing the Mechanism by Online ESI-MS/MS Screening

  摘要：

  A Ru(II)-catalyzed regioselective C-H activation toward hydroxymethylation of beta-carbolines and isoquinolines as effective directing groups has been developed, and the mechanism was probed by using online electrospray ionization-tandem mass spectrometry. The introduction of the hydroxymethyl group in the biologically relevant molecules routed via C-H functionalization remains an important task. Gratifyingly, this protocol draws attention to the regioselective formation of monohydroxymethylated beta-carboline/isoquinoline products exclusively.

  DOI：

  10.1021/acs.joc.9b00454
• 作为产物：
  描述：

  3-(2-Bromo-1-methoxyethyl)-1-(benzenesulfonyl)-2-<(3,4-dimethoxyphenyl)methyl>indole 在 四丁基溴化铵 sodium hydroxide 、 4 A molecular sieve 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 、 paraffin 为溶剂， 反应 27.33h， 生成 1-(3,4-dimethoxyphenyl)-β-carboline
  参考文献：
  名称：

  Preparation of 1-Aryl-.beta.-carbolines

  摘要：

  DOI：

  10.1021/jo00090a046

文献信息

• 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。
• A mild and efficient route to 2-benzyl tryptamine derivatives via ring-opening of β-carbolines
  作者：Fariza Hadjaz、Saïd Yous、Nicolas Lebegue、Pascal Berthelot、Pascal Carato

  DOI：10.1016/j.tet.2008.07.056

  日期：2008.10

  described a mild and easy method, in two steps, by which various benzyl groups were introduced in the C-2 position of tryptamine. The first step consisted on the synthesis of β-carbolines, starting from tryptamine derivatives, by a Pictet–Spengler reaction. Ring-opening of the β-carbolines, by hydrogenation, led to the desired 2-substituted benzyl tryptamine indole products. A supplementary step of alkylation

  我们分两步描述了一种温和而简便的方法，通过该方法，将多种苄基引入色胺的C-2位置。第一步包括通过Pictet-Spengler反应从色胺胺衍生物开始合成β-咔啉。通过氢化使β-咔啉开环，得到所需的2-取代的苄基色胺为吲哚产物。可以实现烷基化的补充步骤，以得到N-烷基-2-取代的苄基色胺。在这些反应过程中，氮原子不需要任何保护步骤。
• Synthesis and structure-activity relationships of asymmetric dimeric β-carboline derivatives as potential antitumor agents
  作者：Liang Guo、Wei Chen、Rihui Cao、Wenxi Fan、Qin Ma、Jie Zhang、Bin Dai

  DOI：10.1016/j.ejmech.2018.02.003

  日期：2018.3

  series of newly asymmetric dimeric β-carbolines with a spacer of 4–6 methylene units between the indole nitrogen and the harmine oxygen were synthesized. Structures of all the novel synthesized compounds were confirmed by their spectral and analytical studies. All of the synthesized compounds were screened for their in vitro cytotoxic activity against nine cancer cell lines. The results revealed that

  合成了一系列新的不对称的二聚β-咔啉，它们在吲哚氮和氨苄基氧之间具有一个4-6个亚甲基单元的间隔。通过光谱和分析研究证实了所有新型合成化合物的结构。筛选所有合成的化合物对九种癌细胞系的体外细胞毒活性。结果表明，化合物7c，7o和7s对测试的肿瘤细胞系表现出最高的细胞毒活性，IC 50值小于20μM。还评估了所选化合物在小鼠中的急性毒性和抗肿瘤功效，并且化合物7o表现出有效的抗肿瘤活性，肿瘤抑制率超过40％。伤口愈合试验显示了HT-29细胞运动性的特定损伤，这提示了化合物7o的抗转移潜力。此外，化合物7o在鸡绒膜尿囊膜（CAM）分析中具有明显的血管生成抑制作用。初步的结构-活性关系（SAR）分析表明：（1）吲哚环N 9位的3-苯基丙基取代基是最合适的产生有效细胞毒性剂的基团；（2）间隔物长度影响抗肿瘤能力，并且四个亚甲基单元是更有利的。
• Synthesis and biological evaluation of novel <i>N</i>⁹-heterobivalent β-carbolines as angiogenesis inhibitors
  作者：Liang Guo、Qin Ma、Wei Chen、Wenxi Fan、Jie Zhang、Bin Dai

  DOI：10.1080/14756366.2018.1497619

  日期：2019.1.1

  Abstract A series of novel N9-heterobivalent β-carbolines has been synthesized. All the novel compounds were tested for their anticancer activity against six tumour cell lines in vitro. Among these molecules, compounds 5b, and 5w exhibited strong cytotoxic activities with IC50 value of lower than 20 μM. Acute toxicities and antitumor efficacies of the selected compounds in mice were also evaluated

  抽象的 已经合成了一系列新颖的N 9-杂二价β-咔啉。测试了所有这些新化合物对六种肿瘤细胞的体外抗癌活性。在这些分子中，化合物5b和5w表现出强大的细胞毒性活性，IC 50值低于20μM。还评估了所选化合物在小鼠中的急性毒性和抗肿瘤功效，化合物5b和5w在肉瘤180和Lewis肺癌动物模型中显示出超过40％的肿瘤抑制率。初步的结构-活性关系（SAR）分析表明：（1）C 1-甲基化和C 7-甲氧基化有助于增加活性；（2）在β-咔啉核心的位置1上的3-吡啶基或2-噻吩基取代基，以及在另一个β-咔啉环上的芳基取代基可能对这类化合物的细胞毒性作用有害。对初步作用机理的研究表明，化合物5b在鸡绒膜尿囊膜（CAM）分析中具有明显的血管生成抑制作用。
• Cu-catalyzed mild and efficient oxidation of THβCs using air: application in practical total syntheses of perlolyrine and flazin
  作者：Bo Zheng、Tien Ha Trieu、Tian-Zhuo Meng、Xia Lu、Jing Dong、Qiang Zhang、Xiao-Xin Shi

  DOI：10.1039/c7ra13434g

  日期：——

  friendliness, mildness, very good tolerance of functional groups, high yielding and easy experiment operation. In addition, this new methodology was successfully applied in the efficient and practical total syntheses of β-carboline alkaloids perlolyrine and flazin.

  开发了一种通过Cu( II ) 催化氧化 1,2,3,4-四氢-β-咔啉 (THβCs)合成芳香族 β-咔啉的温和、高效和环保的方法，其中空气 (O 2 )用作清洁氧化剂。该方法具有环境友好、温和、官能团耐受性好、收率高、实验操作简单等优点。此外，该新方法成功应用于高效实用的β-咔啉生物碱perlolyrine和flalazin的全合成。