In this work, a rapid and high yield synthetic method for N-(4-fluorophenyl)-1-(pyrrolidine-1-carbonyl) cyclopropane-1-carboxamide (8) was established. The target compound 8 was synthesized from the commercially available 1-(methoxycarbonyl) cyclopropane-1-carboxylic acid (5) via multi-step nucleophilic substitution reaction and ester hydrolysis. The structure of the target compound was confirmed by 1H NMR and MS spectrum. The total yield of the three steps was 48.8%.
REFERENCES
1.
Obstetrics and Gynecology Branch of Chinese Medical Association Obstetrics and Gynecology Branch
. Guidelines for prevention and treatment of postpartum hemorrhage
. Chinese Journal of Obstetrics and Gynecology
, 2014
, 49
(9
): 641
–646
.2.
Mcguire
S.
World Cancer Report 2014. Geneva, Switzerland: World Health Organization, International Agency for Research on Cancer, WHO Press, 2015
. Advances in Nutrition
, 2016
, 7
(2
): 418
–419
.3.
Aliebrahimi
S.
, Montasser
S. K.
, Ostad
S. N.
, et al. Identification of Phytochemicals Targeting c-Met Kinase Domain using Consensus Docking and Molecular Dynamics Simulation Studies
. Cell Biochemistry & Biophysics
, 2017
: 1
–11
.4.
Zhai
X.
, Bao
G.
, Wang
L.
, et al. Design, synthesis and biological evaluation of novel 4-phenoxy-6, 7-disubstituted quinolines possessing (thio) semicarbazones as c-Met kinase inhibitors
. Bioorganic & medicinal chemistry
, 2016
, 24
(6
): 1331
–1345
.5.
Maroun
C.R.
, Rowlands
T.
The Met receptor tyrosine kinase: a key player in oncogenesis and drug resistance
. Pharmacol Ther
, 2014
, 142
(3
): 316
–338
.6.
Baljevic
M.
, Zaman
S.
, Baladandayuthapani
V.
, et al. Phase II study of the c-MET inhibitor tivantinib (ARQ 197) in patients with relapsed or relapsed/refractory multiple myeloma
. Annals of hematology
, 2017
, 96
(6
): 977
–985
.7.
Lv
P. C.
, Wang
Z. C.
, Zhu
H. L.
Recent advances in the design and synthesis of c-Met inhibitors as anticancer agents (2014-present
). Current medicinal chemistry
, 2017
, 24
(1
): 57
–64
.8.
Kim
H. J.
, Jung
M. H.
, Kim
H.
, et al. Synthesis and antiproliferative activity of pyrrolo[3,2-b]pyridine derivatives against melanoma
. Bioorganic & Medicinal Chemistry Letters
, 2010
, 20
(1
): 413
–417
.9.
You
W.
, Sennino
B.
, Williamson
C. W.
, et al. VEGF and c-Met blockade amplify angiogenesis inhibition in pancreatic islet cancer
. Cancer Research
, 2011
, 71
(14
): 4758
–4768
.10.
Y.
Kataoka
, T.
Mukohara
, H.
Tomioka
, et al., Foretinib (GSK1363089), a multikinase inhibitor of MET and VEGFRs, inhibits growth of gastric cancer cell lines by blocking inter-receptor tyrosine kinase networks
. Investigational New Drugs
, 2012
, 30
(4
): 1352
–1360
.11.
Zhao
Y.
, Zhang
J.
, Zhuang
R.
, et al. Synthesis and evaluation of a series of pyridine and pyrimidine derivatives as type II c-Met inhibitors
. Bioorganic & Medicinal Chemistry
, 2017
, 25
(12
): 3195
–3205
.12.
Qiang
H.
, Gu
W.
, Huang
D.
, et al. Design, synthesis and biological evaluation of 4-aminopyrimidine-5-cabaldehyde oximes as dual inhibitors of c-Met and VEGFR-2
. Bioorganic & Medicinal Chemistry
, 2016
, 24
(16
): 3353
–3358
.
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