ISAM-140

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 450847712

| Name = ISAM-140

| ImageFile = ISAM-140.png

| ImageSize = 260px

| IUPACNames = (±)-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

| OtherNames = ISAM140

| Section1 = {{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=932191-62-3

| PubChem = 17198004

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 12904393

| ChEMBL = 3787197

| IUPHAR_ligand = 11223

| 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)

| InChIKey = NYHLRBMDXQBOIB-UHFFFAOYSA-N

| SMILES=CC1=C(C(N2C3=CC=CC=C3N=C2N1)C4=CC=CO4)C(=O)OC(C)C

}}

| Section2 = {{Chembox Properties

| Formula=C₁₉H₁₉N₃O₃

| MolarMass=337.37

| Appearance=White solid

}}

| Section3 = {{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

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ISAM-140 is a selective non-xanthinic adenosine A_2B receptor antagonist. Discovered in 2016,{{Cite journal |last1=El Maatougui |first1=Abdelaziz |last2=Azuaje |first2=Jhonny |last3=González-Gómez |first3=Manuel |last4=Miguez |first4=Gabriel |last5=Crespo |first5=Abel |last6=Carbajales |first6=Carlos |last7=Escalante |first7=Luz |last8=García-Mera |first8=Xerardo |last9=Gutiérrez-de-Terán |first9=Hugo |last10=Sotelo |first10=Eddy |date=2016-03-10 |title=Discovery of Potent and Highly Selective A 2B Adenosine Receptor Antagonist Chemotypes |url=https://pubs.acs.org/doi/10.1021/acs.jmedchem.5b01586 |journal=Journal of Medicinal Chemistry |language=en |volume=59 |issue=5 |pages=1967–1983 |doi=10.1021/acs.jmedchem.5b01586 |pmid=26824742 |issn=0022-2623|url-access=subscription }} it has a K_i of 3.49 nM on the A_2B receptor and >1000-fold selectivity with respect to the other three adenosine receptor subtypes. It has been shown to help the immune system to attack cancer cells in in vitro assays by rescuing T and NK cell proliferation, cytokine release, and TIL infiltration.{{Cite journal |last1=Tay |first1=Apple Hui Min |last2=Prieto-Díaz |first2=Rubén |last3=Neo |first3=Shiyong |last4=Tong |first4=Le |last5=Chen |first5=Xinsong |last6=Carannante |first6=Valentina |last7=Önfelt |first7=Björn |last8=Hartman |first8=Johan |last9=Haglund |first9=Felix |last10=Majellaro |first10=Maria |last11=Azuaje |first11=Jhonny |date=2022-05-01 |title=A2B adenosine receptor antagonists rescue lymphocyte activity in adenosine-producing patient-derived cancer models |journal=Journal for ImmunoTherapy of Cancer |language=en |volume=10 |issue=5 |pages=e004592 |doi=10.1136/jitc-2022-004592 |issn=2051-1426 |pmid=35580926|pmc=9115112 |doi-access=free }}