2-bromo-5-(2-isopropoxy-4-nitrophenyl)furan | 1413920-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-5-(2-isopropoxy-4-nitrophenyl)furan
• 英文别名: 2-Bromo-5-(4-nitro-2-propan-2-yloxyphenyl)furan；2-bromo-5-(4-nitro-2-propan-2-yloxyphenyl)furan
• CAS: 1413920-98-5
• 化学式: C₁₃H₁₂BrNO₄
• 分子量: 326.147
• InChiKey: UJXBESZLLPVBNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-bromo-5-(2-isopropoxy-4-nitrophenyl)furan 在 四(三苯基膦)钯 、 10% Pd/C 、 氢气 、 sodium carbonate 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 24.0h， 生成
  参考文献：
  名称：

  Antileishmanial bis-arylimidamides: DB766 analogs modified in the linker region and bis-arylimidamide structure–activity relationships

  摘要：

  Analogs of the lead antileishmanial bis-arylimidamide DB766 were prepared that possess unsymmetrical substitutions on the diphenylfuran linker, and an additional compound was synthesized that contains isopropoxy groups meta to the central furan. These agents all displayed nanomolar in vitro potency against intracellular Leishmania with selectivity indexes >100 compared to J774 macrophages. While the unsymmetrical analogs were toxic to mice when given ip at 30 mg/kg/day, the compound bearing the meta isopropoxy groups was well tolerated by mice and showed activity in a murine model of visceral leishmaniasis when administered ip at 30 mg/kg/day for five days. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.037
• 作为产物：
  描述：

  1-bromo-2-isopropoxy-4-nitrobenzene 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， 生成 2-bromo-5-(2-isopropoxy-4-nitrophenyl)furan
  参考文献：
  名称：

  单芳基酰胺类抗疟药的合成及药理评价

  摘要：

  含有两个吡啶基酰胺基末端基团（bis-AIA）的丙烯酰胺（AIA）化合物具有出色的体外抗霉菌活性，领先的bis-AIA DB766（2,5-bis [2-（2-异丙氧基）-4-（2-吡啶基）吡啶）氨基苯基]呋喃）口服时在内脏利什曼病模型中很活跃。合成了18个包含一个吡啶基酰亚胺酰胺单端基团（mono-AIA）的化合物，并评估了其抗疟药的潜力。这些化合物中的六个对细胞内利什曼原虫和亚马逊利什曼原虫均表现出亚微摩尔效价与J774巨噬细胞细胞系相比，这些化合物中的三种对寄生虫的选择性指数也达到25或更高。当以100 mg / kg / day的剂量口服5天时，化合物1b（N-（3-异丙氧基-4-（5-苯基呋喃-2-基）苯基）吡啶甲酰亚胺酰胺甲磺酸盐）可降低46％的肝寄生虫病。L. donovani感染的小鼠。因此，单-AIA是用于抗衰老药物开发的一类新的候选分子。

  DOI：

  10.1016/j.bmcl.2016.03.082

文献信息

• [EN] ANTI-FUNGAL TREATMENT<br/>[FR] TRAITEMENT ANTIFONGIQUE
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：WO2018045106A1

  公开（公告）日：2018-03-08

  Provided are compounds, methods, and pharmaceutical compositions useful for treatment of fungal infections, e.g., aspergillosis, candidiasis, cryptococcosis, histoplasmosis, and the like. For example, the pharmaceutical composition may include a pharmaceutically acceptable carrier or excipient, and a compound represented by Ar— C(=NR1)NR2— A---X— Y— Het2 and pharmaceutically acceptable salts thereof. Ar may be an optionally substituted aryl or nitrogen- containing heteroaryl. R1 and R2 may independently be H, optionally substituted C1-C6 aikyi, or optionally substituted C3-C6 cyeloalkyi. A may be a bond or an optionally substituted linking moiety comprising 1, 2, or 3 rings. Each ring in the optionally substituted linking moiety may independently be one of: aryl, cyeloalkyi, heterocycloalkyl, and heteroaryl. X may be O, S, amide, or a bond. Y may be optionally substituted C1-C10 alkyi or optionally substituted C2-C10 alkenyl. Het2 may be an optionally substituted five-membered nitrogen-containing heteroaromatic ring comprising 1, 2, or 3 ring heteroatoms.

  提供了用于治疗真菌感染的化合物、方法和药物组合物，例如曲霉病、念珠菌感染、隐球菌病、组织胞浆菌病等。例如，药物组合物可以包括药用可接受载体或赋形剂，以及由Ar—C(=NR1)NR2—A---X—Y—Het2表示的化合物及其药用可接受的盐。Ar可以是可选择取代的芳基或含氮的杂环芳基。R1和R2可以独立地是H、可选择取代的C1-C6烷基或可选择取代的C3-C6环烷基。A可以是键或包含1、2或3个环的可选择取代的连接基。可选择取代的连接基中的每个环可以独立地是以下之一：芳基、环烷基、杂环烷基和杂芳基。X可以是O、S、酰胺或键。Y可以是可选择取代的C1-C10烷基或可选择取代的C2-C10烯基。Het2可以是可选择取代的含五个成员的含氮杂芳环，其中包括1、2或3个环杂原子。
• [EN] ANTI-PARASITIC COMPOUNDS<br/>[FR] COMPOSÉS ANTIPARASITAIRES
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：WO2018045104A1

  公开（公告）日：2018-03-08

  Provided are compounds, methods, and pharmaceutical compositions useful for treatment of parasites, e.g., Leishmania. For example, the compound may he represented by Ar—C(=NR1)NR2—A—X—Y—Het2, and pharmaceutically acceptable salts thereof. Ar may be an optionally substituted, aryl or nitrogen-containing heteroaryl. R1 and R2 may independently represent H, optionally substituted C1-C6 alkyl, or optionally substituted C3-C6 cycloalkyl. A may be a bond or an optionally substituted linking moiety comprising 1, 2, or 3 rings. Each ring in the optionally substituted linking moiety may independently be one of: aryl, cycloalkyl, heterocycloalkyl, and heteroaryl. X may be O, S, amide, or a bond. Y may be optionally substituted C1-C14 alkyl or optionally substituted C2-C14 alkenyl. Het2 may be an optionally substituted five-membered nitrogen-containing heteroaromatic ring comprising 1, 2, or 3 ring heteroatoms.

  提供了一些化合物、方法和药物组合物，用于治疗寄生虫，例如利什曼虫。例如，该化合物可以表示为Ar—C(=NR1)NR2—A—X—Y—Het2，及其药学上可接受的盐。Ar可以是可选择取代的芳基或含氮的杂芳基。R1和R2可以独立表示H、可选择取代的C1-C6烷基或可选择取代的C3-C6环烷基。A可以是一个键或一个可选择取代的连接基，包括1、2或3个环。可选择取代的连接基中的每个环可以独立地是以下之一：芳基、环烷基、杂环烷基和杂芳基。X可以是O、S、酰胺或一个键。Y可以是可选择取代的C1-C14烷基或可选择取代的C2-C14烯基。Het2可以是一个可选择取代的含有5个成员的含氮杂芳环，包括1、2或3个环杂原子。
• Antileishmanial bis-arylimidamides: DB766 analogs modified in the linker region and bis-arylimidamide structure–activity relationships
  作者：Carolyn S. Reid、Abdelbasset A. Farahat、Xiaohua Zhu、Trupti Pandharkar、David W. Boykin、Karl A. Werbovetz

  DOI：10.1016/j.bmcl.2012.06.037

  日期：2012.11

  Analogs of the lead antileishmanial bis-arylimidamide DB766 were prepared that possess unsymmetrical substitutions on the diphenylfuran linker, and an additional compound was synthesized that contains isopropoxy groups meta to the central furan. These agents all displayed nanomolar in vitro potency against intracellular Leishmania with selectivity indexes >100 compared to J774 macrophages. While the unsymmetrical analogs were toxic to mice when given ip at 30 mg/kg/day, the compound bearing the meta isopropoxy groups was well tolerated by mice and showed activity in a murine model of visceral leishmaniasis when administered ip at 30 mg/kg/day for five days. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and pharmacological evaluation of mono-arylimidamides as antileishmanial agents
  作者：Xiaohua Zhu、Abdelbasset A. Farahat、Meena Mattamana、April Joice、Trupti Pandharkar、Elizabeth Holt、Moloy Banerjee、Jamie L. Gragg、Laixing Hu、Arvind Kumar、Sihyung Yang、Michael Zhuo Wang、David W. Boykin、Karl A. Werbovetz

  DOI：10.1016/j.bmcl.2016.03.082

  日期：2016.5

  (bis-AIAs) possess outstanding in vitro antileishmanial activity, and the frontrunner bis-AIA DB766 (2,5-bis[2-(2-isopropoxy)-4-(2-pyridylimino)aminophenyl]furan) is active in visceral leishmaniasis models when given orally. Eighteen compounds containing a single pyridylimidamide terminal group (mono-AIAs) were synthesized and evaluated for their antileishmanial potential. Six of these compounds exhibited

  含有两个吡啶基酰胺基末端基团（bis-AIA）的丙烯酰胺（AIA）化合物具有出色的体外抗霉菌活性，领先的bis-AIA DB766（2,5-bis [2-（2-异丙氧基）-4-（2-吡啶基）吡啶）氨基苯基]呋喃）口服时在内脏利什曼病模型中很活跃。合成了18个包含一个吡啶基酰亚胺酰胺单端基团（mono-AIA）的化合物，并评估了其抗疟药的潜力。这些化合物中的六个对细胞内利什曼原虫和亚马逊利什曼原虫均表现出亚微摩尔效价与J774巨噬细胞细胞系相比，这些化合物中的三种对寄生虫的选择性指数也达到25或更高。当以100 mg / kg / day的剂量口服5天时，化合物1b（N-（3-异丙氧基-4-（5-苯基呋喃-2-基）苯基）吡啶甲酰亚胺酰胺甲磺酸盐）可降低46％的肝寄生虫病。L. donovani感染的小鼠。因此，单-AIA是用于抗衰老药物开发的一类新的候选分子。