PMID- 30658235
OWN - NLM
STAT- MEDLINE
DCOM- 20200203
LR  - 20200203
IS  - 1090-2120 (Electronic)
IS  - 0045-2068 (Linking)
VI  - 85
DP  - 2019 Apr
TI  - Orobanone analogues from acid-promoted aromatization rearrangement of curcumol 
      inhibit hypoxia-inducible factor-1 (HIF-1) in cell-based reporter assays.
PG  - 357-363
LID - S0045-2068(18)31089-7 [pii]
LID - 10.1016/j.bioorg.2019.01.013 [doi]
AB  - In this paper, the mechanism of orobanone analogues formation via aromatization 
      rearrangement of curcumol was minutely explored. Aromatization of curcumol with 
      acetone under acidic condition was selected as the model reaction. The formation 
      of a stable aromatic system was the driving force for this reaction. Based on the 
      model reaction, other four new orobanone analogues were prepared through curcumol 
      reacting with different carbonyl compounds. The results showed that the stability 
      of carbocation, which was generated from the carbonyl compounds, and the steric 
      hindrance were main factors affecting the aromatization. We also synthesized the 
      analogue of aromaticane B using compound 2. In vitro anti-proliferative activity 
      of some derivatives were tested by MTT assay. Two derivatives showed weak 
      anti-tumor effect on two cancer cell lines (HepG2 and MCF7) under normoxia. Four 
      orobanone analogue 2, 5, 6 and 9 significantly inhibited hypoxia-induced HIF-1 
      luciferase reporter activity in HeLa cells with the IC(50) values of 13.6, 6.6, 
      2.4 and 18.2 muM, respectively.
CI  - Copyright (c) 2019 Elsevier Inc. All rights reserved.
FAU - Li, Yue-Qing
AU  - Li YQ
AD  - School of Pharmaceutical Science and Technology, Dalian University of Technology, 
      No. 2 Linggong Road, Dalian 116024, China.
FAU - Li, Guang-Zhe
AU  - Li GZ
AD  - School of Pharmaceutical Science and Technology, Dalian University of Technology, 
      No. 2 Linggong Road, Dalian 116024, China. Electronic address: 
      liguangzhe@dlut.edu.cn.
FAU - Dong, Yi
AU  - Dong Y
AD  - School of Pharmaceutical Science and Technology, Dalian University of Technology, 
      No. 2 Linggong Road, Dalian 116024, China.
FAU - Ma, Xu
AU  - Ma X
AD  - School of Pharmaceutical Science and Technology, Dalian University of Technology, 
      No. 2 Linggong Road, Dalian 116024, China.
FAU - Dong, Hui-Juan
AU  - Dong HJ
AD  - School of Pharmaceutical Science and Technology, Dalian University of Technology, 
      No. 2 Linggong Road, Dalian 116024, China.
FAU - Wu, Qian-Qian
AU  - Wu QQ
AD  - School of Pharmaceutical Science and Technology, Dalian University of Technology, 
      No. 2 Linggong Road, Dalian 116024, China.
FAU - Zhao, Wei-Jie
AU  - Zhao WJ
AD  - School of Pharmaceutical Science and Technology, Dalian University of Technology, 
      No. 2 Linggong Road, Dalian 116024, China; State Key Laboratory of Fine 
      Chemicals, Dalian University of Technology, No. 2 Linggong Road, Dalian 116024, 
      China. Electronic address: zyzhao@dlut.edu.cn.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20190110
PL  - United States
TA  - Bioorg Chem
JT  - Bioorganic chemistry
JID - 1303703
RN  - 0 (Antineoplastic Agents)
RN  - 0 (Hypoxia-Inducible Factor 1)
RN  - 0 (Sesquiterpenes)
RN  - 9190RTN07X (curcumol)
SB  - IM
MH  - Antineoplastic Agents/chemical synthesis/pharmacology
MH  - Cell Hypoxia/physiology
MH  - Cell Line, Tumor
MH  - Cell Proliferation/drug effects
MH  - Humans
MH  - Hypoxia-Inducible Factor 1/*antagonists & inhibitors/genetics
MH  - Sesquiterpenes/chemical synthesis/*pharmacology
MH  - Transcription, Genetic/drug effects
OTO - NOTNLM
OT  - Acid catalysis
OT  - Aromatization
OT  - Curcumol
OT  - HIF-1 transcription
OT  - Orobanone
EDAT- 2019/01/19 06:00
MHDA- 2020/02/06 06:00
CRDT- 2019/01/19 06:00
PHST- 2018/09/28 00:00 [received]
PHST- 2018/12/29 00:00 [revised]
PHST- 2019/01/06 00:00 [accepted]
PHST- 2019/01/19 06:00 [pubmed]
PHST- 2020/02/06 06:00 [medline]
PHST- 2019/01/19 06:00 [entrez]
AID - S0045-2068(18)31089-7 [pii]
AID - 10.1016/j.bioorg.2019.01.013 [doi]
PST - ppublish
SO  - Bioorg Chem. 2019 Apr;85:357-363. doi: 10.1016/j.bioorg.2019.01.013. Epub 2019 
      Jan 10.