5-methoxy-2,2-dimethyl-6-propionyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one | 461694-94-0

• 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-methoxy-2,2-dimethyl-6-propionyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one
• 英文别名: 5-Methoxy-2,2-dimethyl-6-propanoyl-10-propyl-pyrano[2,3-f]chromen-8-one；5-methoxy-2,2-dimethyl-6-propanoyl-10-propylpyrano[2,3-f]chromen-8-one
• CAS: 461694-94-0
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: FLLSDSZVVPVYOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methoxy-2,2-dimethyl-6-propionyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one 在 sodium tetrahydroborate 、 氨 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 6-(1-Amino-propyl)-5-methoxy-2,2-dimethyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one
  参考文献：
  名称：

  Pyranocoumarin, a novel anti-TB pharmacophore: Synthesis and biological evaluation against Mycobacterium tuberculosis

  摘要：

  Pyranocoumarin compounds were identified to embody a novel and unique pharmacophore for anti-TB activity. A systematic approach was taken to investigate the structural characteristics. Focused libraries of compounds were synthesized and evaluated for their anti-TB activity in primary screening assays. Compounds shown to be active were further determined for MIC and MBC values. Three of the four bactericidal compounds (16, 17c, and 18f) were amino derivatives, with MIC values of 16 mu g/mL and respective MBC values of 32, 32, and 64 mu g/mL. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.017
• 作为产物：
  描述：

  5-hydroxy-2,2-dimethyl-10-propyl-6-propionyl-2H,8H-pyrano[2,3-f]chromen-8-one 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到5-methoxy-2,2-dimethyl-6-propionyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one
  参考文献：
  名称：

  Pyranocoumarin, a novel anti-TB pharmacophore: Synthesis and biological evaluation against Mycobacterium tuberculosis

  摘要：

  Pyranocoumarin compounds were identified to embody a novel and unique pharmacophore for anti-TB activity. A systematic approach was taken to investigate the structural characteristics. Focused libraries of compounds were synthesized and evaluated for their anti-TB activity in primary screening assays. Compounds shown to be active were further determined for MIC and MBC values. Three of the four bactericidal compounds (16, 17c, and 18f) were amino derivatives, with MIC values of 16 mu g/mL and respective MBC values of 32, 32, and 64 mu g/mL. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.017

文献信息

• Pyranocoumarin compounds as a novel pharmacophore with anti-TB activity
  申请人：——

  公开号：US20030083369A1

  公开（公告）日：2003-05-01

  The present invention relates to compounds and compositions useful in treating or preventing conditions and diseases related to Mycobacterium infection, and methods of use directed thereto.

  本发明涉及用于治疗或预防与分枝杆菌感染相关的疾病和状况的化合物和组合物，以及相应的使用方法。
• PYRANOCOUMARIN COMPOUNDS AS A NOVEL PHARMACOPHORE WITH ANTI-TB ACTIVITY
  申请人：Sarawak Medichem Pharmaceuticals, Inc.

  公开号：EP1379529A2

  公开（公告）日：2004-01-14
• US6670383B2
  申请人：——

  公开号：US6670383B2

  公开（公告）日：2003-12-30
• [EN] PYRANOCOUMARIN COMPOUNDS AS A NOVEL PHARMACOPHORE WITH ANTI-TB ACTIVITY<br/>[FR] COMPOSES PYRANOCOUMARINIQUES UTILISES EN TANT QUE NOUVEAU PHARMACOPHORE AYANT UNE ACTIVITE ANTI-TB
  申请人：SARAWAK MEDICHEM PHARMACEUTICALS INC

  公开号：WO2002074777A2

  公开（公告）日：2002-09-26

  The present invention relates to compounds according to formula (I) or a pharmaceutical acceptable salt thereof: (formula I) wherein R1 is alkyl, alkenyl, alkynyl, aryl, OH, or NH2; R2 is selected from H, alkyl, alkenyl, alkynyl, aryl and can optionally form a 4 to 7-membered ring with R3; R3 is selected from H, alkyl, alkenyl, alkynyl, aryl and can optionally form a 4 to 7-membered ring with R2; R4 is selected from H, alkyl, alkenyl, akynyl, aryl and can optionally form 4 to 7-membered ring with R5; R5 is selected from H, alkyl,alkenyl, alkynyl, aryl, and can optionally form 4 to 7-membered ring with R4; and R6 is selected from the group consisting of =O, OH, =NH, NH2, SH, P(O)nHm substituted imines, and substituted amines, wherein n is 2-4 and m is 1-3; with the proviso that only one of either R2 and R3 or R4 and R5 optionally form a 6-membered ring, resulting in a compound of formula (I) comprising three fused 6-membered rings, and compositions useful in treating or preventing conditions and diseases related to Mycobacterium infection, and methods of use directed thereto.
• Pyranocoumarin, a novel anti-TB pharmacophore: Synthesis and biological evaluation against Mycobacterium tuberculosis
  作者：Ze-Qi Xu、Krzysztof Pupek、William J. Suling、Livia Enache、Michael T. Flavin

  DOI：10.1016/j.bmc.2006.02.017

  日期：2006.7

  Pyranocoumarin compounds were identified to embody a novel and unique pharmacophore for anti-TB activity. A systematic approach was taken to investigate the structural characteristics. Focused libraries of compounds were synthesized and evaluated for their anti-TB activity in primary screening assays. Compounds shown to be active were further determined for MIC and MBC values. Three of the four bactericidal compounds (16, 17c, and 18f) were amino derivatives, with MIC values of 16 mu g/mL and respective MBC values of 32, 32, and 64 mu g/mL. (c) 2006 Elsevier Ltd. All rights reserved.