From Wikipedia, the free encyclopedia
ISAM-140
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Names
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IUPAC names
(±)-Isopropyl 4-(Furan-2-yl)-2-methyl-1,4-dihydrobenzo-[4,5]imidazo[1,2-a]pyrimidine-3-carboxylate,
4-(2-Furanyl)-4,10-dihydro-2-methyl-pyrimido[1,2-a]benzimidazole-3-carboxylic acid 1-methylethyl ester
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Other names
ISAM140
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Identifiers
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ChEMBL
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ChemSpider
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InChI=1S/C19H19N3O3/c1-11(2)25-18(23)16-12(3)20-19-21-13-7-4-5-8-14(13)22(19)17(16)15-9-6-10-24-15/h4-11,17H,1-3H3,(H,20,21) Key: NYHLRBMDXQBOIB-UHFFFAOYSA-N
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CC1=C(C(N2C3=CC=CC=C3N=C2N1)C4=CC=CO4)C(=O)OC(C)C
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Properties
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C19H19N3O3
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Molar mass
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337.37
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Appearance
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White solid
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
ISAM-140 is a selective non-
xanthinic
adenosine
A2B
receptor
atagonist. Discovered in 2016,
[1] has a
Ki of 3.49 nM in
A2B
receptor and >1000-fold selectivity with respect to the other three
adenosine receptor subtypes. It has been shown to help immune system to attack
cancer cells in in vitro assays, by rescuing
T and
NK cell proliferation,
cytokine release and
TIL infiltration.
[2]
References
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^ El Maatougui, Abdelaziz; Azuaje, Jhonny; González-Gómez, Manuel; Miguez, Gabriel; Crespo, Abel; Carbajales, Carlos; Escalante, Luz; García-Mera, Xerardo; Gutiérrez-de-Terán, Hugo; Sotelo, Eddy (2016-03-10).
"Discovery of Potent and Highly Selective A 2B Adenosine Receptor Antagonist Chemotypes". Journal of Medicinal Chemistry. 59 (5): 1967–1983.
doi:
10.1021/acs.jmedchem.5b01586.
ISSN
0022-2623.
PMID
26824742.
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^ Tay, Apple Hui Min; Prieto-Díaz, Rubén; Neo, Shiyong; Tong, Le; Chen, Xinsong; Carannante, Valentina; Önfelt, Björn; Hartman, Johan; Haglund, Felix; Majellaro, Maria; Azuaje, Jhonny (2022-05-01).
"A2B adenosine receptor antagonists rescue lymphocyte activity in adenosine-producing patient-derived cancer models". Journal for ImmunoTherapy of Cancer. 10 (5): e004592.
doi:
10.1136/jitc-2022-004592.
ISSN
2051-1426.
PMC
9115112.
PMID
35580926.