5,7-Dihydroxy-8-carboxaldehyde-4-propyl-2H-1-benzopyran-2-one

• 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: 5,7-Dihydroxy-8-carboxaldehyde-4-propyl-2H-1-benzopyran-2-one
• 英文别名: DDE213；5,7-dihydroxy-2-oxo-4-propyl-2H-chromene-8-carbaldehyde；5,7-dihydroxy-2-oxo-4-propylchromene-8-carbaldehyde
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: ZAJHTCIZKOYEAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 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：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7-Dihydroxy-8-carboxaldehyde-4-propyl-2H-1-benzopyran-2-one 在 盐酸 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 22.0h， 生成 8-nitro-4-propyl-5-(2-(pyrrolidin-1-yl)ethoxy)-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
• 作为产物：
  描述：

  5,7-二羟基-4-丙基香豆素 以84的产率得到5,7-Dihydroxy-8-carboxaldehyde-4-propyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  J. Org. Chem. 1995, 60, 2964-2965

  摘要：

  DOI：

文献信息

• Detecting <i>Mycobacterium Tuberculosis</i> using a nitrofuranyl calanolide–trehalose probe based on nitroreductase Rv2466c
  作者：Xueyuan Li、Pengfei Geng、Xiaoqiao Hong、Zhaogang Sun、Gang Liu

  DOI：10.1039/d1cc05187c

  日期：——

  NFC-Tre labels single cells of mycobacteria under various stress conditions, including nonreplicating BCG, intracellular BCG and Mtb within sputum samples from patients.

  NFC-Tre可以在各种压力条件下对分枝杆菌的单个细胞进行标记，包括非复制性BCG、细胞内BCG以及患者痰样本中的Mtb。
• Scaffold-hopping strategy toward calanolides with nitrogen-containing heterocycles
  作者：Xiao-Yong Guo、Gang Liu

  DOI：10.1016/j.cclet.2013.03.007

  日期：2013.4

  (+)-Calanolide A was the first natural product identified as an active agent against HIV-1 and Mycobacterium tuberculosis (Mtb). In devising a scaffold-hopping strategy of structure modification of (+)-calanolide A, we focused on the synthesis of calanolides by replacing ring D with various five or six membered nitrogen-containing heterocycles, hoping to get further understanding of the structure-activity relationship. (C) 2013 Gang Liu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  （+)-Calanolide A是首个被确认为对HIV-1和结核杆菌（Mtb）有效的天然产物。在设计针对(+)-calanolide A的结构改进方案时，我们采用了“结构跳板”策略，专注于通过替代环D来合成各种新型的含氮杂环（五元或六元），这有助于进一步揭示其构效关系。 (C) 2013 Gang Liu. 本文由Elsevier B.V.代表中国化学会出版。保留所有权利。
• Modified calanolides incorporated with furan-2-nitro mimics against Mycobacterium tuberculosis
  作者：Zijie Liu、Xiaoyong Guo、Gang Liu

  DOI：10.1016/j.bmcl.2015.01.046

  日期：2015.3

  (+)-Calanolide A was identified as an active agent against both HIV-1 and Mycobacterium tuberculosis (Mtb). We modified Ring D of calanolide compounds with furan-2-nitro mimics and obtained 15 compounds. After in vitro tests, two compounds were shown to be active against replicating (R) Mtb, but not against non-replicating (NR) Mtb. Further optimization for potent candidates against both R Mtb and NR Mtb will result from this research. (C) 2015 Elsevier Ltd. All rights reserved.

  (+)-川芎嗪A被鉴定为对抗HIV-1和结核分枝杆菌（Mtb）的活性剂。我们对川芎嗪类化合物的环D进行修饰，采用了呋喃-2-硝基的模拟物，获得了15种化合物。经过体外测试，其中两种化合物对复制型（R）结核分枝杆菌表现出活性，但对非复制型（NR）结核分枝杆菌无活性。本研究为进一步优化针对R型和NR型结核分枝杆菌的高效候选药物奠定了基础。（C）2015金佰利有限公司版权所有。
• Synthesis of optically active calanolides A and B and enantiomers and
  申请人：The University of Tennessee Research Corporation

  公开号：US05608085A1

  公开（公告）日：1997-03-04

  A method of synthesis of the four optically active stereoisomers of calanolide A and B which produces the compounds in high yields and in a high degree of purity.

  一种合成卡拉诺利德A和B的四个光学活性立体异构体的方法，可高产并高度纯净地产生化合物。
• [EN] SYNTHESIS OF OPTICALLY ACTIVE CALANOLIDES A AND B AND ENANTIOMERS AND RELATED COMPOUNDS<br/>[FR] SYNTHESE DE CALANOLIDES A ET B OPTIQUEMENT ACTIFS, D'ENANTIOMERES ET DE COMPOSES CONNEXES
  申请人：THE UNIVERSITY OF TENNESSEE RESEARCH CORPORATION

  公开号：WO1996026934A1

  公开（公告）日：1996-09-06

  (EN) A method of synthesis of the four optically active stereoisomers of calanolide A and B which produces the compounds in high yields and in a high degree of purity.(FR) Procédé de synthèse des quatre stéréo-isomères optiquement actifs des calanolides A et B, permettant une production à haut rendement de composés d'une grande pureté.

  一种合成calanolide A和B的四种光学活性立体异构体的方法，该方法可以高产高纯度地合成这些化合物。