ISAM-140
Names
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
Other names
ISAM140
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • 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
  • CC1=C(C(N2C3=CC=CC=C3N=C2N1)C4=CC=CO4)C(=O)OC(C)C
Properties
C19H19N3O3
Molar mass 337.37
Appearance White solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

  1. ^ 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.
  2. ^ 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.
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