132994-04-8

Basic information

• Product Name: ETHYL 2-AMINO-1-CYANO-5,6,7,8-TETRAHYDROINDOLIZINE-3-CARBOXYLATE
• Synonyms: ETHYL 2-AMINO-1-CYANO-5,6,7,8-TETRAHYDROINDOLIZINE-3-CARBOXYLATE
• CAS NO: 132994-04-8
• Molecular Formula: C₁₂H₁₅N₃O₂
• Molecular Weight: 233.27
• Mol File: 132994-04-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ETHYL 2-AMINO-1-CYANO-5,6,7,8-TETRAHYDROINDOLIZINE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-AMINO-1-CYANO-5,6,7,8-TETRAHYDROINDOLIZINE-3-CARBOXYLATE(132994-04-8)
• EPA Substance Registry System: ETHYL 2-AMINO-1-CYANO-5,6,7,8-TETRAHYDROINDOLIZINE-3-CARBOXYLATE(132994-04-8)

Safety Data

• Hazardous Substances Data: 132994-04-8(Hazardous Substances Data)

Upstream product

• 78807-02-0 2-dicyanomethylidene-2,3,4,5-tetrahydro-1H,6H-pyridine 
• 105-36-2 ethyl bromoacetate 
• 5693-62-9 2,3,4,5-tetrahydro-6-methoxypyridine 
• 675-20-7 piperidin-2-one 

Downstream Products

• 676334-81-9 4-(4-phenethylpiperazin-1-yl)-6,7,8,9-tetrahydropyrimido[4,5-b]-indolizine-10-carbonitrile 
• 731824-15-0 4-(4-phenylpiperazin-1-yl)-6,7,8,9-tetrahydropyrimido[4,5-b]-indolizine-10-carbonitrile 
• 132994-15-1 4-benzylamino-5,6-tetramethylene-7-ethoxycarbonylpyrrolo<3,4-d>pyrimidine 
• 132994-11-7 3,4-dihydro-3-benzyl-7-cyano-5,6-tetramethylenepyrrolo<3,2-d>pyrimidin-4-one 
• 132994-07-1 5,6,7,8-tetrahydro-2-(N,N-dimethylaminomethylene)amino-3-ethoxycarbonyl-1-cyanoindolizine 

Relevant articles and documents

Pyrrolopyrimidine Derivatives as Novel Inhibitors of Multidrug Resistance-Associated Protein 1 (MRP1, ABCC1)

Five series of pyrrolo[3,2-d]pyrimidines were synthesized and evaluated with respect to potency and selectivity toward multidrug resistance-associated protein 1 (MRP1, ABCC1). This transport protein is a major target to overcome multidrug resistance in cancer patients. We investigated differently substituted pyrrolopyrimidines using the doxorubicin selected and MRP1 overexpressing small cell lung cancer cell line H69 AR in a calcein AM and daunorubicin cell accumulation assay. New compounds with high potency and selectivity were identified. Piperazine residues at position 4 bearing large phenylalkyl side chains proved to be beneficial for MRP1 inhibition. Its replacement by an amino group led to decreased activity. Aliphatic and aliphatic-aromatic variations at position 5 and 6 revealed compounds with IC50 values in high nanomolar range. All investigated compounds had low affinity toward P-glycoprotein (P-gp, ABCB1). Pyrrolopyrimidines with small substituents showed moderate inhibition against breast cancer resistance protein (BCRP, ABCG2).

SYNTHESIS AND BIOLOGICAL ACTIVITY OF CONDENSED PYRROLOPYRIMIDINES

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