dihydroparthenolide | 2513-76-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: dihydroparthenolide
• 英文别名: 11βH,13-dihydroparthenolide；11β,13-dihydroparthenolide；11,13-dihydroparthenolide；11beta,13-Dihydroparthenolide；(1S,2R,4R,7E,11S,12S)-4,8,12-trimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one
• CAS: 2513-76-0
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: GSVWPONNFJXHJL-IOCBBESTSA-N

物化性质

• 熔点：
  137-139 °C
• 沸点：
  383.3±42.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 dihydroparthenolide 在 对甲苯磺酸 作用下， 反应 6.0h， 以25 mg的产率得到
  参考文献：
  名称：

  Antimycobacterial evaluation of germacranolides in honour of professor G.H. Neil Towers 75th birthday

  摘要：

  The minimum inhibitory concentrations (MIC) against Mycobacterium tuberculosis and M. avium of parthenolide, costunolide, 1 (10)-epoxycostunolide and other germacranolide-type sesquiterpene lactones and derivatives were determined by use of a radiorespirometric bioassay. Structure-activity relationship studies with natural and semisynthetic sesquiterpene lactones suggested that the alpha-methylene-gamma-lactone moiety is an essential, but not sufficient, structural requirement for significant in vitro activity against M. tuberculosis and M. avium. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00253-2
• 作为产物：
  描述：

  小白菊内酯 在 1% Pd/C 、 氢气 作用下， 生成 dihydroparthenolide
  参考文献：
  名称：

  Aminoparthenolides as novel anti-leukemic agents: Discovery of the NF-κB inhibitor, DMAPT (LC-1)

  摘要：

  A series of aminoparthenolide analogs (6-37) were synthesized and evaluated for their anti-leukemic activity. Eight compounds exhibited good anti-leukemic activity with LD50's in the low mu M range (1.5-3.0 mu M). Compounds 16, 24 and 30 were the most potent compounds in the series, causing greater than 90% cell death at 10 mu M concentration against primary AML cells in culture, with LD50 values of 1.7, 1.8 and 1.6 mu M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.092

文献信息

• PARODI, FELIX J.;FRONCZEK, FRANK R.;FISCHER, NIKOLAUS H., J. NATUR. PROD., 52,(1989) N, C. 554-566
  作者：PARODI, FELIX J.、FRONCZEK, FRANK R.、FISCHER, NIKOLAUS H.

  DOI：——

  日期：——
• USE OF PARTHENOLIDE DERIVATIVES AS ANTILEUKEMIC AND CYTOTOXIC AGENTS
  申请人：University of Kentucky

  公开号：US20190231790A1

  公开（公告）日：2019-08-01

  The present invention provides compounds of the formula (I) wherein: X 1 , X 2 and X 3 are heteroatoms; R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are independently selected from H, halo, —OH, —NO 2 , —CN and optionally substituted aliphatic, cycloalkyl, heterocycloalkyl, aryl or heteroaryl; and Z is optionally substituted C 1-8 straight-chained or branched aliphatic, optionally containing 1 or more double or triple bonds, wherein one or more carbons are optionally replaced by R* wherein R* is optionally substituted cycloalkyl, heterocycloalkyl, aryl or heteroaryl; an amino acid residue, H, —CN, —C(O)—, —C(O)C(O)—, —C(O)NR 1 —, —C(O)NR 1 NR 2 —, —C(O)O—, —OC(O)—, —NR 1 CO 2 —, —O—, —NR 1 C(O)NR 2 —, —OC(O)NR 1 —, —NR 1 C(O)—, —S—, —SO—, —SO 2 —, —NR 1 —, —SO 2 NR 1 —, —NR 1 R 2 , or —NR 1 SO 2 —, wherein R 1 and R 2 are independently selected from H and optionally substituted aliphatic, cycloalkyl, heterocycloalkyl, aryl or heteroaryl; or where R* is NR 1 R 2 , R 1 and R 2 optionally together with the nitrogen atom form an optionally substituted 5-12 membered ring, said ring optionally comprising 1 or more heteroatoms or a group selected from —CO—, —SO—, —SO 2 — and —PO—; or a pharmaceutically acceptable salt, ester or prodrug thereof.
• Aminoparthenolides as novel anti-leukemic agents: Discovery of the NF-κB inhibitor, DMAPT (LC-1)
  作者：Sundar Neelakantan、Shama Nasim、Monica L. Guzman、Craig T. Jordan、Peter A. Crooks

  DOI：10.1016/j.bmcl.2009.05.092

  日期：2009.8

  A series of aminoparthenolide analogs (6-37) were synthesized and evaluated for their anti-leukemic activity. Eight compounds exhibited good anti-leukemic activity with LD50's in the low mu M range (1.5-3.0 mu M). Compounds 16, 24 and 30 were the most potent compounds in the series, causing greater than 90% cell death at 10 mu M concentration against primary AML cells in culture, with LD50 values of 1.7, 1.8 and 1.6 mu M. (C) 2009 Elsevier Ltd. All rights reserved.
• Antimycobacterial evaluation of germacranolides in honour of professor G.H. Neil Towers 75th birthday
  作者：Nikolaus H. Fischer、Tiansheng Lu、Charles L. Cantrell、José Castañeda-Acosta、Leovigildo Quijano、Scott G. Franzblau

  DOI：10.1016/s0031-9422(98)00253-2

  日期：1998.9

  The minimum inhibitory concentrations (MIC) against Mycobacterium tuberculosis and M. avium of parthenolide, costunolide, 1 (10)-epoxycostunolide and other germacranolide-type sesquiterpene lactones and derivatives were determined by use of a radiorespirometric bioassay. Structure-activity relationship studies with natural and semisynthetic sesquiterpene lactones suggested that the alpha-methylene-gamma-lactone moiety is an essential, but not sufficient, structural requirement for significant in vitro activity against M. tuberculosis and M. avium. (C) 1998 Elsevier Science Ltd. All rights reserved.