3-amino-4-(1H-pyrrol-1-yl)benzonitrile | 251649-45-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-amino-4-(1H-pyrrol-1-yl)benzonitrile
• 英文别名: 1-(2-amino-4-cyanophenyl)-1H-pyrrole；3-amino-4-pyrrol-1-ylbenzonitrile
• CAS: 251649-45-3
• 化学式: C₁₁H₉N₃
• 分子量: 183.213
• InChiKey: BAZDVRVFNORIFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-amino-4-(1H-pyrrol-1-yl)benzonitrile 在 铁粉 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 反应 9.0h， 生成 4-methylpyrrolo[1,2-a]quinoxaline-7-carbonitrile
  参考文献：
  名称：

  Synthesis and in vitro evaluation of 4-trichloromethylpyrrolo[1,2-a]quinoxalines as new antiplasmodial agents

  摘要：

  Thanks to a preliminary in vitro screening of several CCl3-substituted-nitrogen containing heterocycles belonging to our chemical library, the 2-trichloromethylquinoxaline scaffold appeared to be of potential interest for developing new antiplasmodial agents. Then, combining these experimental results to the antimalarial properties reported for various pyrrolo[1,2-a]quinoxaline derivatives, an original series of fifteen 7-substituted-4-trichoromethylpyrrolo[1,2-a]quinoxalines was synthesized in a 4 to 5 reaction steps pathway. All molecules were evaluated in vitro toward both their antiplasmodial activity on the K1 multi-resistant Plasmodium falciparum strain and their cytotoxicity on the HepG2 human cell line. Thus, 3 hit molecules were identified, displaying IC50 values in the micromolar range and low cytotoxicity values, reaching good selectivity indexes, in comparison with the reference drugs chloroquine and doxycycline. Structure-activity relationship studies showed that the pyrrolo[1,2-a]quinoxaline scaffold can support selective antiplasmodial activity when substituted at position 4 by a CCl3 group. However, substitution at position 7 of the same scaffold is neither beneficial for cytotoxicity nor favourable for the solubility in the biological media.

  DOI：

  10.1016/j.ejmech.2014.06.014
• 作为产物：
  描述：

  4-氨基-3-硝基苯甲腈 在 铁粉 、 氯化铵 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 6.0h， 生成 3-amino-4-(1H-pyrrol-1-yl)benzonitrile
  参考文献：
  名称：

  1-(2-氨基苯基)吡咯电化学氧化脱氢环化与醚裂解合成吡咯并[1,2-a]喹喔啉衍生物

  摘要：

  通过电化学氧化还原反应，包括 C(sp 3 )–H 键的官能化以及 C–C 和 C–N 的构建，获得了一系列吡咯并[1,2- a ]喹喔啉衍生物，产率中等至良好债券。在该原子经济反应中，THF既用作反应物又用作溶剂，H 2是唯一的副产物。

  DOI：

  10.1039/d3ob01867a

文献信息

• [EN] NOVEL PROTEIN KINASE MODULATORS<br/>[FR] MODULATEURS INÉDITS DES PROTÉINES KINASES
  申请人：CYLENE PHARMACEUTICALS INC

  公开号：WO2010135571A1

  公开（公告）日：2010-11-25

  The invention provides compounds that inhibit selected kinases (Pirn, Fit and/or CK2 kinases) and compositions containing such compounds. These compounds and compositions are useful for treating proliferative disorders such as cancer, as well as other kinase-associated conditions including inflammation, pain, and certain infections and immunological disorders.

  该发明提供了抑制特定激酶（Pirn、Fit和/或CK2激酶）的化合物，以及含有这些化合物的组合物。这些化合物和组合物可用于治疗增生性疾病，如癌症，以及其他与激酶相关的疾病，包括炎症、疼痛、某些感染和免疫性疾病。
• Annulation of 1-(2-Aminoaryl)pyrroles, Ethers with Elemental Sulfur To Give 1,3,6-Benzothiadiazepine Derivatives through Double C–S Bond Formation and C–O Cleavage of Ethers
  作者：Jie Zhang、Chuwen Song、Linfeng Sheng、Ping Liu、Peipei Sun

  DOI：10.1021/acs.joc.8b03187

  日期：2019.2.15

  An efficient three-component reaction of 1-(2-aminoaryl)pyrroles, ethers, and elemental sulfur for constructing N-heterocycle-fused 1,3,6-benzothiadiazepines under transition-metal-free conditions has been developed. Ethers act as both reactants and solvent in this reaction. The method proceeds efficiently over a broad range of substrates with good functional group tolerance.

  已经开发了一种在无过渡金属的条件下，由1-（2-氨基芳基）吡咯，醚和元素硫组成的高效三组分反应，用于构建N杂环稠合的1,3,6-苯并噻二氮杂ze。醚在该反应中既充当反应物又充当溶剂。该方法可在具有良好官能团耐受性的各种基材上有效地进行。
• <i>N</i>,<i>N</i>-Dimethylformamide as Carbon Synthons for the Synthesis of <i>N</i>-Heterocycles: Pyrrolo/Indolo[1,2-<i>a</i>]quinoxalines and Quinazolin-4-ones
  作者：Shichen Li、Jianing Ren、Chengcheng Ding、Yishou Wang、Chen Ma

  DOI：10.1021/acs.joc.1c02067

  日期：2021.12.3

  N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered that N-methyl and

  N , N-二甲基甲酰胺 (DMF) 作为合成前体，尤其是甲基、酰基和氨基，在杂环合成和功能化中发挥了重要作用。在该协议中，通过使用不含任何金属或过氧化物的元素碘，以中等至良好的收率获得了范围广泛的 pyrrolo/indolo[1,2 - a ]quinoxalines 和 quinazolin-4-ones。我们认为DMF的N-甲基和N-酰基通过不同的机理分别参与并完成反应，这表明DMF的潜力仍有待探索。
• Pyrroloquinoxaline Derivatives as High-Affinity and Selective 5-HT₃ Receptor Agonists:  Synthesis, Further Structure−Activity Relationships, and Biological Studies
  作者：Giuseppe Campiani、Elena Morelli、Sandra Gemma、Vito Nacci、Stefania Butini、Michel Hamon、Ettore Novellino、Giovanni Greco、Alfredo Cagnotto、Mara Goegan、Luigi Cervo、Fabio Dalla Valle、Claudia Fracasso、Silvio Caccia、Tiziana Mennini

  DOI：10.1021/jm990151g

  日期：1999.10.1

  [(3)H]zacopride binding. The SAR studies detailed herein delineated a number of structural features required for improving affinity. Some of the ligands were employed as "molecular yardsticks" to probe the spatial dimensions of the lipophilic pockets L1, L2, and L3 in the 5-HT(3) receptor cleft, while the 7-OH pyrroloquinoxaline analogue was designed to investigate hydrogen bonding with a putative receptor site

  描述了一系列新型吡咯并喹喔啉和杂芳族相关衍生物的合成，药理评价和构效关系（SAR）。新的吡咯并喹喔啉相关配体在大鼠皮层，表达高密度5-HT（3）受体的组织中以及在NG108-15细胞上进行了测试，并在低纳摩尔或亚纳摩尔范围内表现出IC（50）值，方法是通过抑制[（3）H] zacopride结合。本文详述的SAR研究描述了改善亲和力所需的许多结构特征。一些配体被用作“分子尺度”，以探测5-HT（3）受体裂隙中亲脂性口袋L1，L2和L3的空间尺寸，而7-OH吡咯并喹喔啉类似物被设计用于研究与可能与5-羟色胺羟基相互作用的假定受体位点H1的氢键作用。最活跃的吡咯并喹喔啉衍生物对5-HT（3）受体显示亚纳摩尔亲和力。在功能研究中（[[14] C]胍在NG108-15杂化细胞中的体外积累试验），大多数受试化合物均显示出明确的5-HT（3）激动剂特性，而另一些则为部分激动剂。关于5-HT（3）亲和力
• Photoredox-Catalyzed Radical Cascade Reaction To Synthesize Fluorinated Pyrrolo[1,2-<i>d</i>]benzodiazepine Derivatives
  作者：Guifang Lian、Jingyu Li、Ping Liu、Peipei Sun

  DOI：10.1021/acs.joc.9b00937

  日期：2019.7.19

  A new photoredox-catalyzed cascade reaction is described to access fluorinated pyrrolo[1,2-d]benzodiazepine derivatives under mild conditions. In this process, single electron transfer (SET) between the excited state photocatalyst fac-Ir(ppy)3 and ethyl bromodifluoroacetate initiated the regioselective radical addition to a wide range of 2-(1H-pyrrol-1-yl) anilines or indol-substituted anilines, followed

  描述了一种新的光氧化还原催化的级联反应，可在温和条件下获得氟化吡咯并[1,2- d ]苯并二氮杂卓衍生物。在此过程中，激发态光催化剂fac -Ir（ppy）3和溴二氟乙酸乙酯之间的单电子转移（SET）引发了区域选择性自由基加成到2-（1 H-吡咯-1-基）苯胺或吲哚的范围大取代的苯胺，然后进行另一个SET工艺和分子内酰胺化。