2-Nitro-2,3-dihydrobenzofuran | 117266-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2-Nitro-2,3-dihydrobenzofuran
• 英文别名: 2-nitro-2,3-dihydro-1-benzofuran
• CAS: 117266-64-5
• 化学式: C₈H₇NO₃
• 分子量: 165.148
• InChiKey: ONUWYQDAYBJQPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-Chloro-2-nitroethenyl)phenol 在 sodium tetrahydroborate 、 silica gel 、 potassium carbonate 作用下， 以 氯仿 、 异丙醇 、 丙酮 为溶剂， 反应 6.0h， 生成 2-Nitro-2,3-dihydrobenzofuran
  参考文献：
  名称：

  A Convenient and General Route to 2-Nitro-2,3-dihydrobenzofurans

  摘要：

  本研究以 2-(2-氯-2-硝基乙烯基)苯酚为起点，采用简单易行的两步法制备了迄今未知的标题化合物。 报告还描述了在合成过程中作为中间体分离出来的新型 2-(2-氯-2-硝基乙基)苯酚。

  DOI：

  10.1055/s-1988-27567

文献信息

• Synthetic Calanolides with Bactericidal Activity against Replicating and Nonreplicating <i>Mycobacterium tuberculosis</i>
  作者：Purong Zheng、Selin Somersan-Karakaya、Shichao Lu、Julia Roberts、Maneesh Pingle、Thulasi Warrier、David Little、Xiaoyong Guo、Steven J. Brickner、Carl F. Nathan、Ben Gold、Gang Liu

  DOI：10.1021/jm4019228

  日期：2014.5.8

  It is urgent to introduce new drugs for tuberculosis to shorten the prolonged course of treatment and control drug-resistant Mycobacterium tuberculosis (Mtb). One strategy toward this goal is to develop antibiotics that eradicate both replicating (R) and nonreplicating (NR) Mtb. Naturally occurring (+)-calanolide A was active against R-Mtb. The present report details the design, synthesis, antimycobacterial activities, and structure-activity relationships of synthetic calanolides. We identified potent dual-active nitro-containing calanolides with minimal in vitro toxicity that were cidal to axenic Mtb and Mtb in human macrophages, while sparing Gram-positive and -negative bacteria and yeast. Two of the nitrobenzofuran-containing lead compounds were found to be genotoxic to mammalian cells. Although genotoxicity precluded clinical progression, the profound, selective mycobactericidal activity of these calanolides will be useful in identifying pathways for killing both R- and NR-Mtb, as well as in further structure-based design of more effective and drug-like antimycobacterial agents.
• A Convenient and General Route to 2-Nitro-2,3-dihydrobenzofurans
  作者：Daniel Dauzonne、René Royer

  DOI：10.1055/s-1988-27567

  日期：——

  A facile and general two-step preparation of the hitherto unknown title compounds is reported starting from 2-(2-chloro-2-nitroethenyl)phenols. The novel 2-(2-chloro-2-nitroethyl)phenols isolated as intermediates in the synthesis are described.

  本研究以 2-(2-氯-2-硝基乙烯基)苯酚为起点，采用简单易行的两步法制备了迄今未知的标题化合物。 报告还描述了在合成过程中作为中间体分离出来的新型 2-(2-氯-2-硝基乙基)苯酚。