CMF-019

CMF-019
Identifiers
	IUPAC name (3S)-5-methyl-3-[[1-pentan-3-yl-2-(thiophen-2-ylmethyl)benzimidazole-5-carbonyl]amino]hexanoic acid;
CAS Number	1586787-08-7;
PubChem CID	73442763;
Chemical and physical data
Formula	C25H33N3O3S
Molar mass	455.62 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(CC)N1C2=C(C=C(C=C2)C(=O)N[C@@H](CC(C)C)CC(=O)O)N=C1CC3=CC=CS3;
	InChI InChI=1S/C25H33N3O3S/c1-5-19(6-2)28-22-10-9-17(25(31)26-18(12-16(3)4)14-24(29)30)13-21(22)27-23(28)15-20-8-7-11-32-20/h7-11,13,16,18-19H,5-6,12,14-15H2,1-4H3,(H,26,31)(H,29,30)/t18-/m0/s1; Key:VCQKKZXFASLXAH-SFHVURJKSA-N;

CMF-019 is a drug which is a selective, small-molecule agonist for the apelin receptor. It is used in research into treatment for heart failure.^[1]^[2]^[3]

References

^ Read C, Fitzpatrick CM, Yang P, Kuc RE, Maguire JJ, Glen RC, et al. (September 2016). "Cardiac action of the first G protein biased small molecule apelin agonist". Biochemical Pharmacology. 116: 63–72. doi:10.1016/j.bcp.2016.07.018. PMC 5012889. PMID 27475715.
^ Trifonov L, Afri M, Palczewski K, Korshin EE, Gruzman A (2018). "An Expedient Synthesis of CMF-019: (S)-5-Methyl-3-{1-(pentan-3-yl)-2-(thiophen-2-ylmethyl)-1H-benzo[d]imidazole-5-carboxamido}hexanoic Acid, a Potent Apelin Receptor (APJ) Agonist". Medicinal Chemistry. 14 (7): 688–694. doi:10.2174/1573406414666180412154952. PMC 6993063. PMID 29651942.
^ Narayanan S, Vasukuttan V, Rajagopal S, Maitra R, Runyon SP (February 2020). "Identification of potent pyrazole based APELIN receptor (APJ) agonists". Bioorganic & Medicinal Chemistry. 28 (4) 115237. doi:10.1016/j.bmc.2019.115237. PMC 7055011. PMID 31948845.

[1] Read C, Fitzpatrick CM, Yang P, Kuc RE, Maguire JJ, Glen RC, et al. (September 2016). "Cardiac action of the first G protein biased small molecule apelin agonist". Biochemical Pharmacology. 116: 63–72. doi:10.1016/j.bcp.2016.07.018. PMC 5012889. PMID 27475715.

[2] Trifonov L, Afri M, Palczewski K, Korshin EE, Gruzman A (2018). "An Expedient Synthesis of CMF-019: (S)-5-Methyl-3-{1-(pentan-3-yl)-2-(thiophen-2-ylmethyl)-1H-benzo[d]imidazole-5-carboxamido}hexanoic Acid, a Potent Apelin Receptor (APJ) Agonist". Medicinal Chemistry. 14 (7): 688–694. doi:10.2174/1573406414666180412154952. PMC 6993063. PMID 29651942.

[3] Narayanan S, Vasukuttan V, Rajagopal S, Maitra R, Runyon SP (February 2020). "Identification of potent pyrazole based APELIN receptor (APJ) agonists". Bioorganic & Medicinal Chemistry. 28 (4) 115237. doi:10.1016/j.bmc.2019.115237. PMC 7055011. PMID 31948845.

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[2]

[3]

See also

References