ethyl 9-(4-fluorobenzyl)-β-carboline-3-carboxylate | 737817-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 9-(4-fluorobenzyl)-β-carboline-3-carboxylate
• 英文别名: ethyl 9-(4-fluorobenzyl)-9H-β-carboline-3-carboxylate；Ethyl 9-(4-fluorobenzyl)-9h-beta-carboline-3-carboxylate；ethyl 9-[(4-fluorophenyl)methyl]pyrido[3,4-b]indole-3-carboxylate
• CAS: 737817-62-8
• 化学式: C₂₁H₁₇FN₂O₂
• 分子量: 348.377
• InChiKey: ZZLRNLUGBXSFDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 9-(4-fluorobenzyl)-β-carboline-3-carboxylate 在 manganese(IV) oxide 、 锂硼氢 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.0h， 生成 9-(4-fluorobenzyl)-β-carboline-3-carbaldehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of piperazine group-linked bivalent β-carbolines as potential antitumor agents

  摘要：

  一系列具有3-亚甲基单元之间的哌嗪基间隔的二价β-咔啉类化合物被合成，并评估了它们的体外细胞毒活性。化合物7e和7g表现出强大的细胞毒活性。

  DOI：

  10.1039/c5md00312a
• 作为产物：
  描述：

  2,3,4,9-四氢-1H-beta-咔啉-3-甲酸 在 氯化亚砜 、 sodium hydride 、 sulfur 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 ethyl 9-(4-fluorobenzyl)-β-carboline-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of piperazine group-linked bivalent β-carbolines as potential antitumor agents

  摘要：

  一系列具有3-亚甲基单元之间的哌嗪基间隔的二价β-咔啉类化合物被合成，并评估了它们的体外细胞毒活性。化合物7e和7g表现出强大的细胞毒活性。

  DOI：

  10.1039/c5md00312a

文献信息

• Design, Synthesis, and Biological Evaluation of Novel N-Acylhydrazone Bond Linked Heterobivalent β-Carbolines as Potential Anticancer Agents
  作者：Chen、Guo、Ma、Chen、Fan、Zhang

  DOI：10.3390/molecules24162950

  日期：——

  Utilizing a pharmacophore hybridization approach, we have designed and synthesized a novel series of 28 new heterobivalent β-carbolines. The in vitro cytotoxic potential of each compound was evaluated against the five cancer cell lines (LLC, BGC-823, CT-26, Bel-7402, and MCF-7) of different origin—murine and human, with the aim of determining the potency and selectivity of the compounds. Compound 8z

  利用药效团杂交方法，我们设计并合成了一系列新的 28 种新型异二价 β-咔啉。评估了每种化合物对不同来源（鼠类和人）的五种癌细胞系（LLC、BGC-823、CT-26、Bel-7402 和 MCF-7）的体外细胞毒性潜力，目的是确定化合物的效力和选择性。化合物 8z 显示出抗肿瘤活性，半数最大抑制浓度 (IC50) 值为 9.9 ± 0.9、8.6 ± 1.4、6.2 ± 2.5、9.9 ± 0.5 和 5.7 ± 1.2 µM，对测试的五种癌细胞系。此外，使用鸡绒毛尿囊膜 (CAM) 体内模型研究了化合物 8z 对血管生成过程的影响。在 5 μM 的浓度下，化合物 8z 显示出对血管生成的积极影响。
• [EN] HIV-INTEGRASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS FOR THEIR USE<br/>[FR] INHIBITEURS DE VIH-INTEGRASE, COMPOSITIONS PHARMACEUTIQUES ET METHODES D'UTILISATION DESDITS INHIBITEURS
  申请人：PFIZER

  公开号：WO2004067531A1

  公开（公告）日：2004-08-12

  Beta-carboline hydroxamic acid compounds represented by formula (I) and formula (lb) are described, wherein: R1, R2, R3, R4, R5, and R6 are independently selected from hydrogen, halogen, C1_C6 alkyl, aikoxy C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, -ORc, -NO2, and -N(Rc)2, each Rc is Independently selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, and C2-Ca alkynyl; R7 Is C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl, all of which are optionally substituted by one or more substituents independently selected from halogen, C1-C6 alkyl, C2-C6 alkenyl; C2-C6 alkynyl, aryl, cycloalkyl, heterocycioalkyl, and heteroaryl, wherein said aryl, cydoalkyi, and heterocycloalkyl are optionally substituted with one or more substituents independently selected from halogen, C1-C6 alkyl, C2-C6 alkenyl, and C2-C6 alkynyl; R8 and R9 are independently selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, and C2-C6 aikynyl, wherein said alkyl, alkenyl, and alkynyl are optionally substituted with one or more substituents independently selected from halogen, aryl, cycloalkyl, heterocycloalkyl, and heteroaryl group, wherein said aryl, cycloalkyl, and heterocycloalkyl are optionally substituted with one or more substituents independently selected from halogen, C1-C6 alkyl, C2-C6 alkenyl, and C2-C6 alkynyl. The beta-carboline hydroxamic acid compounds and compositions containing those compounds may be used to inhibit or modulate the activity of HIV integrase enzyme and to treat HIV integrase-mediated diseases and conditions.

  描述了由式（I）和式（lb）表示的β-咔啉羟肟酸化合物，其中：R1、R2、R3、R4、R5和R6分别独立地选自氢、卤素、C1-C6烷基、氧基C1-C6烷基、C2-C6烯基、C2-C6炔基、-ORc、-NO2和-N(Rc)2，每个Rc独立地选自氢、C1-C6烷基、C2-C6烯基和C2-Ca炔基；R7为C1-C6烷基、C2-C6烯基或C2-C6炔基，这些基都可以选择性地被一个或多个取代基取代，这些取代基独立地选自卤素、C1-C6烷基、C2-C6烯基、C2-C6炔基、芳基、环烷基、杂环烷基和杂芳基，其中所述芳基、环烷基和杂环烷基可以选择性地被一个或多个取代基取代，这些取代基独立地选自卤素、C1-C6烷基、C2-C6烯基和C2-C6炔基；R8和R9独立地选自氢、C1-C6烷基、C2-C6烯基和C2-C6炔基，其中所述烷基、烯基和炔基可以选择性地被一个或多个取代基取代，这些取代基独立地选自卤素、芳基、环烷基、杂环烷基和杂芳基，其中所述芳基、环烷基和杂环烷基可以选择性地被一个或多个取代基取代，这些取代基独立地选自卤素、C1-C6烷基、C2-C6烯基和C2-C6炔基。这些β-咔啉羟肟酸化合物和含有这些化合物的组合物可用于抑制或调节HIV整合酶的活性，并用于治疗HIV整合酶介导的疾病和症状。
• HIV-integrase inhibitors, pharmaceutical compositions, and methods for their use
  申请人：Kuki Atsuo

  公开号：US20050165040A1

  公开（公告）日：2005-07-28

  Beta-carboline hydroxamic acid compounds represented by formula (I) are described. The beta-carboline hydroxamic acid compounds and compositions containing those compounds may be used to inhibit or modulate the activity of HIV integrase enzyme and to treat HIV integrase-mediated diseases and conditions.

  由公式（I）表示的β-咔啉羟肟酸化合物被描述。这些β-咔啉羟肟酸化合物和含有这些化合物的组合物可用于抑制或调节HIV整合酶酶的活性，并用于治疗HIV整合酶介导的疾病和症状。
• HIV integrase inhibitors, pharmaceutical compositions and methods for their use
  申请人：Kuki Atsuo

  公开号：US20060122211A1

  公开（公告）日：2006-06-08

  Beta-carboline hydroxamic acid compounds represented by formula (I) are described. The beta-carboline hydroxamic acid compounds and compositions containing those compounds may be used to inhibit or modulate the activity of HIV integrase enzyme and to treat HIV integrase-mediated diseases and conditions.

  本文描述了由公式（I）表示的β-咔啉羟肟酸化合物。这些β-咔啉羟肟酸化合物及含有这些化合物的组合物可用于抑制或调节HIV整合酶酶活性，并用于治疗HIV整合酶介导的疾病和病况。
• Design, synthesis and 3D-QSAR of β-carboline derivatives as potent antitumor agents
  作者：Rihui Cao、Xiangdong Guan、Buxi Shi、Zhiyong Chen、Zhenhua Ren、Wenlie Peng、Huacan Song

  DOI：10.1016/j.ejmech.2010.02.036

  日期：2010.6

  In a continuing effort to develop novel beta-carbolines endowed with better pharmacological profiles, a series of beta-carboline derivatives were designed and synthesized based on the previously developed SARs. Cytotoxicities in vitro of these compounds against a panel of human tumor cell lines were also investigated. The results demonstrated that the N(2)-benzylated beta-carbolinium bromides 56-60 represented the most potent compounds with IC(50) values lower than 10 mu M. The application of 3D-QSAR to these compounds explored the structural basis for their biological activities. CoMFA (q(2) = 0.513, r(2) = 0.862) and CoMSIA (q(2) = 0.503, r(2) = 0.831) models were developed for a set of 47 beta-carbolines. The results indicated that the antitumor pharmacophore of these molecules were marked at position-1, -2, -3, -7 and -9 of beta-carboline ring.