6-(5-溴呋喃-2-基)吡啶-3-甲腈 | 619334-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 6-(5-溴呋喃-2-基)吡啶-3-甲腈
• 英文名称: 6-(5-bromofuran-2-yl)nicotinonitrile
• 英文别名: 6-(5-Bromo-furan-2-yl)-nicotinonitrile；6-(5-bromofuran-2-yl)pyridine-3-carbonitrile
• CAS: 619334-29-1
• 化学式: C₁₀H₅BrN₂O
• 分子量: 249.066
• InChiKey: JMVGDWOYNIKXAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  196 °C
• 沸点：
  335.8±42.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(5-溴呋喃-2-基)吡啶-3-甲腈 在 sodium hydroxide 、 四(三苯基膦)钯 、 盐酸羟胺 、 potassium tert-butylate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  氘标记的 6-[5-(4-脒基苯基)呋喃-2-基]烟脒和 N-烷氧基-6-{5-[4-(N-烷氧基脒基)苯基]-呋喃-2-基}-烟脒的合成

  摘要：

  6-[5-(4-脒基苯基)呋喃-2-基]烟脒-d4(5)由6-[5-(4-氰基苯基)呋喃-2-基]烟腈-d4(3)合成，通过双-O-乙酰氧基-脒肟，然后氢化。化合物 3 由 6-(呋喃-2-基)-烟腈通过与 4-溴苄腈-d4 的 Heck 偶联反应制备，4-溴苄腈-d4 是 1,4-二溴苯-d4 与 Cu(1)CN 的选择性氰化反应产物。氘标记的 N-甲氧基-6-{5-[4-(N-甲氧基-脒基苯基]-呋喃-2-基}-烟脒是通过在氢氧化钠水溶液中用硫酸二甲酯-d6 甲基化它们各自的脒脒来制备的。版权所有 © 2004 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.817
• 作为产物：
  描述：

  2-溴-5-氰基吡啶 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 6-(5-溴呋喃-2-基)吡啶-3-甲腈
  参考文献：
  名称：

  呋喃结构修饰对 DNA 小沟结合和抗原生动物活性影响的研究

  摘要：

  利用 Stille 偶联反应和使用双三甲基甲硅烷基氨基锂对双腈中间体进行酰胺化，制备了抗原生动物剂呋喃啶的新类似物。呋喃的苯基和呋喃部分都被杂环取代，包括噻吩、硒吩、吲哚或苯并咪唑。根据 Δ Tm和 CD 结果，新化合物显示出与 DNA 小沟的强结合。新的类似物在体外和体内也比呋喃胺更有活性。化合物 7a、7b 和 7f通过治愈 75% 的动物显示出最高的体内活性，这值得进一步评估。

  DOI：

  10.1016/j.ejmech.2023.115287

文献信息

• Synthesis and Antiprotozoal Activity of Aza-Analogues of Furamidine
  作者：Mohamed A. Ismail、Reto Brun、Judy D. Easterbrook、Farial A. Tanious、W. David Wilson、David W. Boykin

  DOI：10.1021/jm0302602

  日期：2003.10.1

  6-[5-(4-Amidinophenyl)furan-2-yl]nicotinamidine (8a) was synthesized from 6-[5-(4-cyanophenyl)furan-2-yl]nicotinonitrile (4a), through the bis-O-acetoxyamidoxime followed by hydrogenation. Compound 4a was prepared via selective bromination of 6-(furan-2-yl)nicotinonitrile (2a) with N-bromosuccinimide, followed by Suzuki coupling with 4-cyanophenylboronic acid. In a similar way, diamidines 8b and 8c

  由6- [5-（4-氰基苯基）呋喃-2-基]烟腈（4a）通过双-O-合成6- [5-（4-A氨基苯基）呋喃-2-基]烟酰胺（8a）。乙酰氧基ami肟，然后氢化。通过用N-溴代琥珀酰亚胺对6-（呋喃-2-基）烟腈（2a）进行选择性溴化，然后与4-氰基苯基硼酸进行Suzuki偶联，来制备化合物4a。以类似的方式，分别由二氰基衍生物4c和4d制备二am8b和8c。N-甲氧基-6- [5- [4-（N-甲氧基ami基）苯基]-呋喃-2-基]-烟酰胺（6a）是通过用二甲基硫酸甲酯将二胺肟5a甲基化而制备的。前药6b和6c也通过各自的二mid肟5b和5d的甲基化制备。通过相应的双-O-乙酰氧基酰胺肟合成对称的二am14a，b，然后氢化。通过在2，5-双（三正丁基锡烷基）呋喃与相应的杂芳基卤化物之间进行Stille偶联，可以方便地获得关键化合物11a，b。这些化合物已在体外评估了对罗氏锥虫（T. br）和恶性疟原虫（P
• Dicationic 2,5-diarylfuran aza-analogs as anti-protozoan agents
  申请人：——

  公开号：US20040122015A1

  公开（公告）日：2004-06-24

  A compound of Formula (I): 1 wherein: X is selected from the group consisting of O, S, and NR 17 , where R 17 is hydrogen or lower alkyl; C 1 , C 2 , A, and Y are CH, N, NR 17 , O, or S, wherein C 1 and C 2 are the same or different; D 1 , D 2 , B, and Z are CH, N, or NR 17 wherein D 1 and D 2 are the same or different; provided that B, Z, or both B and Z are not present when A, Y, or both A and Y are O, S, or NR 17 ; R 13 , R 14 , R 15 , R 16 , R 1 and R 8 are selected from the group consisting of H, lower alkyl, halogen, alkoxyl, aryloxyl, aralkoxy and hydroxyl; R 3 and R 6 are each independently selected from the group consisting of H, hydroxy, lower alkyl, cycloalkyl, aryl, aralkyl, alkoxyl, hydroxycycloalkyl, alkoxycycloalkyl, hydroxyalkyl, aminoalkyl, acyloxy, acetoxy, and alkylaminoalkyl; and R 2 , R 4 , R 5 and R 7 are each independently selected from the group consisting of H, lower alkyl, alkoxyalkyl, cycloalkyl, aryl, aralkyl, hydroxyalkyl, aminoalkyl, and alkylaminoalkyl, or R 2 and R 4 together or R 5 and R 7 together represent a C 2 to C 10 alkyl, hydroxyalkyl, or alkylene, or R 3 and R 4 together or R 6 and R 7 together are: 2 wherein n is a number from 1 to 3, and R 9 is H or —CONHR 10 NR 11 R 12 , wherein R 10 is lower alkyl and R 11 and R 12 are each independently selected from the group consisting of H and lower alkyl.

  化合物公式（I）：1其中：X从O，S和NR17组成的群中选择，其中R17是氢或低级烷基；C1，C2，A和Y是CH，N，NR17，O或S，其中C1和C2相同或不同；D1，D2，B和Z是CH，N或NR17，其中D1和D2相同或不同；但是当A，Y或A和Y都是O，S或NR17时，B，Z或B和Z都不存在；R13，R14，R15，R16，R1和R8从H，低级烷基，卤素，烷氧基，芳氧基，芳基烷氧基和羟基中选择；R3和R6各自独立地从H，羟基，低级烷基，环烷基，芳基，芳基烷基，烷氧基，羟基环烷基，烷氧基环烷基，羟基烷基，氨基烷基，酰氧基，乙酰氧基和烷基氨基烷基中选择；R2，R4，R5和R7各自独立地从H，低级烷基，烷氧基烷基，环烷基，芳基，芳基烷基，羟基烷基，氨基烷基和烷基氨基烷基中选择，或者R2和R4一起或R5和R7一起表示C2到C10烷基，羟基烷基或烷基，或者R3和R4一起或R6和R7一起是：2其中n是1到3的数字，R9是H或—CONHR10NR11R12，其中R10是低级烷基，R11和R12各自独立地从H和低级烷基中选择。
• Dicationic compounds which selectively recognize G-quadruplex DNA
  申请人：Wilson W. David

  公开号：US20100249175A1

  公开（公告）日：2010-09-30

  Dicationic compounds that are highly selective for binding G-quadruplex DNA are described. Several compounds exhibit groove binding toward G-quadruplex DNA and in vitro and in vivo activity versus Trypanosoma brucei rhodesiense. The compounds represent novel drugs for the treatment of cancer, malaria, leishmania, and trypanosomiasis.

  本文描述了高度选择性结合G四链体DNA的二阳离子化合物。几种化合物对G四链体DNA表现出凹槽结合的特性，并在体内外显示出对Trypanosoma brucei rhodesiense的活性。这些化合物代表了治疗癌症、疟疾、利什曼病和锥虫病的新型药物。
• Harnessing Heterocycles: Fine-Tuning Furan-Pyridine Amidines for Precision Anticancer Therapy
  作者：H. M. El-Shafeai、E. Abdel-Latif、A. A. Fadda、M. R. Elmorsy、M. A. Ismail

  DOI：10.1134/s1070363224010183

  日期：2024.1

  the smallest HOMO-LUMO gap for analogue 6-[5-(3,4-dichlorophenyl)furan-2-yl]nicotinamidine dihydrochloride (1.91 eV), followed by 6-[5-(2,4-dichlorophenyl)furan-2-yl]nicotinamidine dihydrochloride (1.92 eV), relative to the lead 3,5-dichloro compound I (2.62 eV), suggesting 6-[5-(3,4-dichlorophenyl)furan-2-yl]nicotinamidine dihydrochloride has the highest chemical reactivity among the investigated amidines

  摘要 两种新的二氯苯基呋喃基烟脒区域异构体由相应的二氯苯基呋喃基烟腈用双(三甲基甲硅烷基)氨基锂处理并随后脱保护，然后形成氯化氢盐来制备。采用 6-(5-溴呋喃-2-基)烟腈与二氯苯基硼酸的 Suzuki 偶联条件制备烟腈。计算评估提供了对电子结构和化学反应性的见解。评估了它们针对 9 种组织类型的 60 种癌细胞系的抗增殖活性。 6-[5-(2,4-二氯苯基)呋喃-2-基]烟脒二盐酸盐表现出最高的整体效力，中值 GI 50为 1.65 μM。分子模型显示类似物 6-[5-(3,4-二氯苯基)呋喃-2-基]烟脒二盐酸盐的 HOMO-LUMO 间隙最小 (1.91 eV)，其次是 6-[5-(2,4-二氯苯基)呋喃-2-基]烟脒二盐酸盐 (1.92 eV)，相对于先导 3,5-二氯化合物I (2.62 eV)，表明 6-[5-(3,4-二氯苯基)呋喃-2-基]烟脒二盐酸盐在所研究的脒中具有最
• Synthesis, antimicrobial, and antiproliferative activities of substituted phenylfuranylnicotinamidines
  作者：Mohamed Ismail、Reem Arafa、Magdy Youssef

  DOI：10.2147/dddt.s102128

  日期：——

  This research work deals with the design and synthesis of a series of substituted phenylfuranylnicotinamidines 4a-i. Facile preparation of the target compounds was achieved by Suzuki coupling-based synthesis of the nitrile precursors 3a-i, followed by their conversion to the corresponding nicotinamidines 4a-i utilizing LiN(TMS)(2). The antimicrobial activities of the newly synthesized nicotinamidine derivatives were evaluated against the Gram-negative bacterial strains Escherichia coli and Pseudomonas aeruginosa as well as the Gram-positive bacterial strains Staphylococcus aureus and Bacillus megaterium. The minimum inhibitory concentration values of nicotinamidines against all tested microorganisms were in the range of 10-20 mu M. In specific, compounds 4a and 4b showed excellent minimum inhibitory concentration values of 10 mu M against Staphylococcus aureus bacterial strain and were similar to ampicillin as an antibacterial reference. On the other hand, selected nicotinamidine derivatives were biologically screened for their cytotoxic activities against a panel of 60 cell lines representing nine types of human cancer at a single high dose at National Cancer Institute, Bethesda, MD, USA. Nicotinamidines showing promising activities were further assessed in a five-dose screening assay to determine their compound concentration causing 50% growth inhibition of tested cell (GI(50)), compound concentration causing 100% growth inhibition of tested cell (TGI), and compound concentration causing 50% lethality of tested cell (LC50) values. Structure-activity relationship studies demonstrated that the activity of members of this series can be modulated from cytostatic to cytotoxic based on the substitution pattern/nature on the terminal phenyl ring. The most active compound was found to be 4e displaying a submicromolar GI(50) value of 0.83 mu M, with TGI and LC50 values of 2.51 and 100 mu M, respectively. Finally, the possible underlying mechanism of action of this series of compounds was investigated by determining their nuclease-like DNA degradation ability in addition to their antioxidant power and all monocations proved to be effective in all assays.