9-isopropyl-5-(2-morpholinoethoxy)-8-nitro-4-propyl-2H-furo[2,3-h]chromen-2-one | 1393820-88-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 9-isopropyl-5-(2-morpholinoethoxy)-8-nitro-4-propyl-2H-furo[2,3-h]chromen-2-one
• 英文别名: 9-Isopropyl-5-(2-morpholinoethoxy)-8-nitro-4-propyl-furo[2,3-h]chromen-2-one；5-(2-morpholin-4-ylethoxy)-8-nitro-9-propan-2-yl-4-propylfuro[2,3-h]chromen-2-one
• CAS: 1393820-88-6
• 化学式: C₂₃H₂₈N₂O₇
• 分子量: 444.485
• InChiKey: RFLTTYKWJHKSTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-hydroxy-5-(2-morpholinoethoxy)-2-oxo-4-propyl-2H-chromene-8-carbaldehyde 在 碘苯二乙酸 、 ammonium acetate 、 四丁基碘化铵 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 3.17h， 生成 9-isopropyl-5-(2-morpholinoethoxy)-8-nitro-4-propyl-2H-furo[2,3-h]chromen-2-one
  参考文献：
  名称：

  Synthetic Calanolides with Bactericidal Activity against Replicating and Nonreplicating Mycobacterium tuberculosis

  摘要：

  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.

  DOI：

  10.1021/jm4019228

文献信息

• Iodine(III)-Mediated Tandem Oxidative Cyclization for Construction of 2-Nitrobenzo[<i>b</i>]furans
  作者：Shi-Chao Lu、Pu-Rong Zheng、Gang Liu

  DOI：10.1021/jo301162x

  日期：2012.9.7

  Various 3-alkyl-2-nitrobenzo[b]furans were synthesized from common intermediate 2-(2-nitroethyl)phenols via a hypervalent iodine-induced oxidative cyclization, with good to excellent yields. This facile route is able to efficiently functionalize 2-nitrobenzo[b]furans, which are difficult to obtain by classical methods.

  由普通的中间体2-（2-硝基乙基）苯酚经高价碘诱导的氧化环化反应合成了各种3-烷基-2-硝基苯并[ b ]呋喃，其收率高到极好。这种简便的途径能够有效地官能化2-硝基苯并[ b ]呋喃，这是传统方法难以获得的。