2,5-双(三丁基锡)呋喃

• 分子结构分类: 有机化合物 - 有机金属化合物 - 金属芳基
• 中文名称: 2,5-双(三丁基锡)呋喃
• 英文名称: 2,5-bis(tri-n-butylstannyl)furan
• 英文别名: 2,5-bis(tributylstannyl)furan
• 化学式: C₂₈H₅₆OSn₂
• 分子量: 646.172
• InChiKey: TWUYAXFJUMLGIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.39
• 重原子数：
  31
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-溴-5-硝基三氟甲苯 、 2,5-双(三丁基锡)呋喃 在 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 生成 2,5-bis(4-nitro-2-trifluorophenyl)furan
  参考文献：
  名称：

  The activity of diguanidino and ‘reversed’ diamidino 2,5-diarylfurans versus Trypanosoma cruzi and Leishmania donovani

  摘要：

  The in vitro activity of 20 dicationic molecules containing either diguanidino or reversed amidine cationic groups were evaluated versus Trypanosoma cruzi and Leishmania donovani. The most active compounds were in the reversed amidine series and six exhibited IC50 values of less than 1 mumol versus T. cruzi and five gave similar values versus L. donovani. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00319-6
• 作为产物：
  描述：

  呋喃 、 三丁基氯化锡 在 仲丁基锂 作用下， 生成 2,5-双(三丁基锡)呋喃
  参考文献：
  名称：

  Synthesis and antiparasitic activity of new bis-arylimidamides: DB766 analogs modified in the terminal groups

  摘要：

  Fifteen novel bis-arylimidamide derivatives with various 6-membered (7a-c) and 5-membered (7d-o) heterocyclic rings replacing the terminal pyridyl rings of the lead compound DB766{(2,5-bis[2-i-propoxy-4-(2-pyridylimino)aminophenylfuran]}, were prepared and evaluated versus Trypanosoma cruzi, Leishmania amazonensis, Trypanosoma brucei rhodesiense and Plasmodium falciparum. Compound 7a with pyrimidine replacing the pyridine rings showed good activity versus T. cruzi, T. brucei rhodesiense and P. falciparum (IC50 = 200 nM, 32 nM and 8.5 nM, respectively). Three compounds (7g, 7i, 7j) with thiazole replacing the pyridine rings gave low micromolar (0.17-0.3 μM) IC50 values versus L. amazonensis, however only 7g exhibited an acceptable selectivity index (SI = 27). Compounds 7a, 7j and 7m exhibited potent activity against T. brucei rhodesiense (IC50 = 12-60 nM). Ten of the 15 compounds with pyrimidine, pyrrole, thiazole and imidazole terminal units were highly active against P. falciparum (IC50 = 9-87 nM). Both pyrimidine and pyridine terminal groups are advantageous for anti-T. cruzi activity and several different heterocyclic terminal units are effective versus P. falciparum, both findings merit further investigation.

  DOI：

  10.1016/j.ejmech.2014.06.022

文献信息

• [EN] NOVEL AMIDINE COMPOUNDS FOR TREATING MICROBIAL INFECTIONS<br/>[FR] NOUVEAUX COMPOSES D'AMIDINE DANS LE TRAITEMENT D'INFECTIONS MICROBIENNES
  申请人：UNIV NORTH CAROLINA

  公开号：WO2005033065A1

  公开（公告）日：2005-04-14

  Novel amidine and diamidine compounds are useful in the treatment of microbial infections, including mycobacterial, fungal and protozoal infections. Pharmaceutical formulations comprising these compounds can be used in methods of treating microbial infections.

  新型胍和二胍化合物在治疗微生物感染方面具有重要作用，包括结核菌、真菌和原虫感染。含有这些化合物的药物配方可用于治疗微生物感染的方法。
• 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
• New antiparasitic flexible triaryl diamidines, their prodrugs and aza analogues: Synthesis, in vitro and in vivo biological evaluation, and molecular modelling studies
  作者：Reem K. Arafa、Mohamed A. Ismail、Tanja Wenzler、Reto Brun、Ananya Paul、W. David Wilson、Amira A. Alakhdar、David W. Boykin

  DOI：10.1016/j.ejmech.2021.113625

  日期：2021.10

  Dicationic diamidines have been well established as potent antiparasitic agents with proven activity against tropical diseases like trypanosomiasis and malaria. This work presents the synthesis of new mono and diflexible triaryl amidines (6a-c, 13a,b and 17), their aza analogues (23 and 27) and respective methoxyamidine prodrugs (5, 7, 12a,b, 22 and 26). All diamidines were assessed in vitro against

  双阳离子二脒已被证实是有效的抗寄生虫剂，已证明对锥虫病和疟疾等热带疾病具有活性。这项工作提出新的单和diflexible三芳基脒（合成6A-C ，图13A，B和17），它们的氮杂类似物（23和27）和相应的methoxyamidine前药（5，7，图12A，B，22和26）。所有二脒都在体外对罗得西亚布氏锥虫( T. br ) 和恶性疟原虫( Plasmodium falciparum )进行了评估。P.F. )，它们在纳摩尔水平上显示出有效到中等的活性，对T. br 的IC 50 s = 11-378 nM，对P. f. 的IC 50 s = 4-323 nM 。. 针对T. br STIB900 的体内功效测试表明，单柔性二脒6c是本研究中最有效的衍生物，在 4 × 5 mg/kg 剂量 ip 治疗后，治疗期>60 天，感染小鼠的治愈率为 4/4 . 此外，该系列二脒/聚 (dA-dT)
• A Novel and Convenient Synthesis of ‘Reversed’ Diamidino 2,5-Aryl- and 2,5-Azaheterocycle-Substituted Furans
  作者：David Boykin、Laixing Hu

  DOI：10.1055/s-0029-1216817

  日期：2009.7

  novel and convenient two-step synthesis of ‘reversed’ diamidino 2,5-aryl- and 2,5-azaheterocycle-substituted furans is described. The key step, a Stille cross-coupling reaction between N-(bromoaryl)arenecarboxamidines and 2,5-bis(tri-n-butylstannyl)furan, is reported for the first time. reversed amidines - thioimidates - Stille cross-coupling reaction - furans - N-heterocycles

  描述了一种新颖且方便的两步合成“颠倒的”二mid氨基2,5-芳基-和2,5-氮杂杂环取代的呋喃。首次报道了关键步骤，即N-（溴芳基）芳烃甲am与2,5-双（三-正丁基锡烷基）呋喃之间的Stille交叉偶联反应。 反向am-硫代亚氨酸-斯蒂勒交叉偶联反应-呋喃-N-杂环
• Green Fluorescent Diamidines as Diagnostic Probes for Trypanosomes
  作者：Federica Giordani、Manoj Munde、W. David Wilson、Mohamed A. Ismail、Arvind Kumar、David W. Boykin、Michael P. Barrett

  DOI：10.1128/aac.02024-13

  日期：2014.3

  Light-emitting diode (LED) fluorescence microscopy offers potential benefits in the diagnosis of human African trypanosomiasis and in other aspects of diseases management, such as detection of drug-resistant strains. To advance such approaches, reliable and specific fluorescent markers to stain parasites in human fluids are needed. Here we describe a series of novel green fluorescent diamidines and their suitability as probes with which to stain trypanosomes.

  摘要 发光二极管（LED）荧光显微镜为诊断人类非洲锥虫病和疾病管理的其他方面（如检测耐药菌株）提供了潜在的益处。要推进这些方法，需要可靠而特异的荧光标记物来染色人体液中的寄生虫。在此，我们介绍了一系列新型绿色荧光二脒及其作为探针对锥虫进行染色的适用性。