6-(2-呋喃基)烟腈 | 619334-28-0

• 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-(2-呋喃基)烟腈
• 英文名称: 6-(furan-2-yl)nicotinonitrile
• 英文别名: 6-(2-Furyl)nicotinonitrile；6-(furan-2-yl)pyridine-3-carbonitrile
• CAS: 619334-28-0
• 化学式: C₁₀H₆N₂O
• 分子量: 170.17
• InChiKey: MLVPTQAKBGAZLS-UHFFFAOYSA-N

物化性质

• 熔点：
  114 °C
• 沸点：
  306.2±32.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 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-(2-呋喃基)烟腈 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90.4%的产率得到6-(5-溴呋喃-2-基)吡啶-3-甲腈
  参考文献：
  名称：

  呋喃idine的氮杂类似物的合成及其抗原生动物活性。

  摘要：

  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

  DOI：

  10.1021/jm0302602
• 作为产物：
  描述：

  6-氯-3-氰基吡啶 、 2-(三丁基锡烷基)呋喃 在 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以80.6%的产率得到6-(2-呋喃基)烟腈
  参考文献：
  名称：

  呋喃idine的氮杂类似物的合成及其抗原生动物活性。

  摘要：

  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

  DOI：

  10.1021/jm0302602

文献信息

• Synthesis of deuterium-labelled 6-[5-(4-amidinophenyl)furan-2-yl]nicotinamidine andN-alkoxy-6-{5-[4-(N-alkoxyamidino)phenyl]- furan-2-yl}-nicotinamidines
  作者：Mohamed A. Ismail、David W. Boykin

  DOI：10.1002/jlcr.817

  日期：2004.3.30

  6-[5-(4-Amidinophenyl)furan-2-yl]nicotinamidine-d4 (5) was synthesized from 6-[5-(4-cyanophenyl)furan-2-yl]nicotinonitrile-d4 (3), through the bis-O-acetoxy-amidoxime followed by hydrogenation. Compound 3 was prepared from 6-(furan-2-yl)-nicotinonitrile by a Heck coupling reaction with 4-bromobenzonitrile-d4, a product of selective cyanation reaction of 1,4-dibromobenzene-d4 with Cu(1)CN. Deuterium-labelled

  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.
• 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。
• Novel bichalcophenes and their prodrugs as antiprotozoal agents
  申请人：Tidwell R. Richard

  公开号：US20060293540A1

  公开（公告）日：2006-12-28

  Novel dicationic bichalcophene compounds are described. The presently disclosed novel dicationic bichalcophene compounds exhibit in vitro activity versus Trypanosoma brucei rhodesiense, Plasmodium falciparum , or Leishmania donovani comparable to that of pentamidine and furamidine. Some of the novel dicationic bichalcophene compounds displayed good activity in vivo in a murine model of a Trypanosoma brucei rhodesiense infection.

  本文描述了新型的双阳离子双硫杂环化合物。目前披露的新型双阳离子双硫杂环化合物在体外对Trypanosoma brucei rhodesiense、Plasmodium falciparum或Leishmania donovani的活性与pentamidine和furamidine相当。其中一些新型双阳离子双硫杂环化合物在小鼠Trypanosoma brucei rhodesiense感染模型中表现出良好的活性。
• 5,5'-bis-(4-amidinophenyl)-2,2'-bifuran derivatives and related compounds as antiprotozoal agent and prodrugs thereof
  申请人：The University of North Carolina at Chapel Hill

  公开号：EP1726589B1

  公开（公告）日：2008-10-15
• Heterocyclic Diamidine DNA Ligands as HOXA9 Transcription Factor Inhibitors: Design, Molecular Evaluation, and Cellular Consequences in a HOXA9-Dependant Leukemia Cell Model
  作者：Sabine Depauw、Mélanie Lambert、Samy Jambon、Ananya Paul、Paul Peixoto、Raja Nhili、Laura Marongiu、Martin Figeac、Christelle Dassi、Charles Paul-Constant、Benjamin Billoré、Arvind Kumar、Abdelbasset A. Farahat、Mohamed A. Ismail、Ekaterina Mineva、Daniel P. Sweat、Chad E. Stephens、David W. Boykin、W. David Wilson、Marie-Hélène David-Cordonnier

  DOI：10.1021/acs.jmedchem.8b01448

  日期：2019.2.14

  Most transcription factors were for a long time considered as undruggable targets because of the absence of binding pockets for direct targeting. HOXA9, implicated in acute myeloid leukemia, is one of them. To date, only indirect targeting of HOXA9 expression or multitarget HOX/PBX protein/protein interaction inhibitors has been developed. As an attractive alternative by inhibiting the DNA binding, we selected a series of heterocyclic diamidines as efficient competitors for the HOXA9/DNA interaction through binding as minor groove DNA ligands on the HOXA9 cognate sequence. Selected DB818 and DB1055 compounds altered HOXA9-mediated transcription in luciferase assays, cell survival, and cell cycle, but increased cell death and granulocyte/monocyte differentiation, two main HOXA9 functions also highlighted using transcriptomic analysis of DB818-treated murine Hoxa9-transformed hematopoietic cells. Altogether, these data demonstrate for the first time the propensity of sequence-selective DNA ligands to inhibit HOXA9/DNA binding both in vitro and in a murine Hoxa9-dependent leukemic cell model.