11βH,13-dihydro-13-dimethylaminomicheliolide hydrochloride | 1403357-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 11βH,13-dihydro-13-dimethylaminomicheliolide hydrochloride
• 英文别名: Dimethylaminomicheliolide HCl；(3R,3aS,9R,9aS,9bS)-3-[(dimethylamino)methyl]-9-hydroxy-6,9-dimethyl-3,3a,4,5,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one;hydrochloride
• CAS: 1403357-80-1
• 化学式: C₁₇H₂₇NO₃*ClH
• 分子量: 329.867
• InChiKey: ZKHJWBSQJWCFMA-GMFVQMBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11βH,13-dihydro-13-dimethylaminomicheliolide hydrochloride 以 aq. buffer 为溶剂， 生成 乌心石内酯(木香内酯)
  参考文献：
  名称：

  Guaianolide Sesquiterpene Lactones, a Source To Discover Agents That Selectively Inhibit Acute Myelogenous Leukemia Stem and Progenitor Cells

  摘要：

  Small molecules that can selectively target cancer stem cells (CSCs) remain rare currently and exhibit no common structural features. Here we report a series of guaianolide sesquiterpene lactones (GSLs) and their derivatives that can selectively eradicate acute myelogenous leukemia (AML) stem or progenitor cells. Natural GSL compounds arglabin, an anticancer clinical drug, and micheliolide (MCL), are able to reduce the proportion of AML stem cells (CD34(+)CD38(-)) in primary AML cells. Targeting of AML stem cells is further confirmed by a sharp reduction of colony-forming units of primary AML cells upon MCL treatment. Moreover, DMAMCL, the dimethylamino Michael adduct of MCL, slowly releases MCL in plasma and in vivo and demonstrates remarkable therapeutic efficacy in the nonobese diabetic/severe combined immunodeficiency AML models. These findings indicate that GSL is an ample source for chemical agents against AML stem or progenitor cells and that GSL is potentially highly useful to explore anti-CSC approaches.

  DOI：

  10.1021/jm301064b
• 作为产物：
  描述：

  parthenolide 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 11βH,13-dihydro-13-dimethylaminomicheliolide hydrochloride
  参考文献：
  名称：

  倍半萜内酯类化合物及其衍生物在制备药物中 的用途

  摘要：

  本发明涉及倍半萜内酯类化合物及其衍生物在制备药物中的用途，属于药物技术领域，具体涉及式(I)化合物在制备药物中的用途，特别是在制备治疗类风湿性关节炎、通过抑制癌症干细胞用于治疗癌症的药物中的用途。

  公开号：

  CN103417532B

文献信息

• USES OF SESQUITERPENE LACTONE COMPOUNDS AND THEIR DERIVATIVES IN DRUGS PREPARATION
  申请人：ACCENDATECH

  公开号：US20160367525A1

  公开（公告）日：2016-12-22

  The present invention relates to the uses of sesquiterpene lactone compounds and their derivatives in preparing drugs. It belongs to the field of drug technology, specifically relates to the uses of the compounds of Formula (I) in preparing the drugs, especially the uses in preparing the drugs to treat rheumatoid arthritis and treat cancers through inhibiting cancer stem cells.

  本发明涉及倍半萜内酯化合物及其衍生物在制备药物中的用途。它属于药物技术领域，具体涉及在制备药物中使用式(I)化合物，特别是在制备用于治疗类风湿关节炎和通过抑制癌干细胞治疗癌症的药物中的用途。
• SPHAELACTONE DERIVATIVES, THEIR PHARMACEUTICAL COMPOSITIONS, PREPARATION METHODS AND USES
  申请人：Accendatech

  公开号：EP2562172B1

  公开（公告）日：2016-04-13
• 倍半萜内酯类化合物及其衍生物在制备药物中 的用途
  申请人：天津尚德药缘科技股份有限公司

  公开号：CN103417532B

  公开（公告）日：2016-06-01

  本发明涉及倍半萜内酯类化合物及其衍生物在制备药物中的用途，属于药物技术领域，具体涉及式(I)化合物在制备药物中的用途，特别是在制备治疗类风湿性关节炎、通过抑制癌症干细胞用于治疗癌症的药物中的用途。
• Guaianolide Sesquiterpene Lactones, a Source To Discover Agents That Selectively Inhibit Acute Myelogenous Leukemia Stem and Progenitor Cells
  作者：Quan Zhang、Yaxin Lu、Yahui Ding、Jiadai Zhai、Qing Ji、Weiwei Ma、Ming Yang、Hongxia Fan、Jing Long、Zhongsheng Tong、Yehui Shi、Yongsheng Jia、Bin Han、Wenpeng Zhang、Chuanjiang Qiu、Xiaoyan Ma、Qiuying Li、Qianqian Shi、Haoliang Zhang、Dongmei Li、Jing Zhang、Jianping Lin、Lu-Yuan Li、Yingdai Gao、Yue Chen

  DOI：10.1021/jm301064b

  日期：2012.10.25

  Small molecules that can selectively target cancer stem cells (CSCs) remain rare currently and exhibit no common structural features. Here we report a series of guaianolide sesquiterpene lactones (GSLs) and their derivatives that can selectively eradicate acute myelogenous leukemia (AML) stem or progenitor cells. Natural GSL compounds arglabin, an anticancer clinical drug, and micheliolide (MCL), are able to reduce the proportion of AML stem cells (CD34(+)CD38(-)) in primary AML cells. Targeting of AML stem cells is further confirmed by a sharp reduction of colony-forming units of primary AML cells upon MCL treatment. Moreover, DMAMCL, the dimethylamino Michael adduct of MCL, slowly releases MCL in plasma and in vivo and demonstrates remarkable therapeutic efficacy in the nonobese diabetic/severe combined immunodeficiency AML models. These findings indicate that GSL is an ample source for chemical agents against AML stem or progenitor cells and that GSL is potentially highly useful to explore anti-CSC approaches.