Chemistry:SB-699551

SB-699551
Identifiers
	IUPAC name 3-cyclopentyl-N-[2-(dimethylamino)ethyl]-N-[(4'-([(2-phenylethyl)amino]methyl)-4-biphenylyl)methyl]propanamide;
CAS Number	791789-61-2 ;
PubChem CID	11168182;
ChemSpider	9343277;
UNII	3FN59X9DPR;
Chemical and physical data
Formula	C34H45N3O
Molar mass	511.754 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C2CCCC2CCC(=O)N(CCN(C)C)Cc(cc3)ccc3-c(cc1)ccc1CNCCc4ccccc4;
	InChI InChI=1S/C34H45N3O/c1-36(2)24-25-37(34(38)21-16-28-10-6-7-11-28)27-31-14-19-33(20-15-31)32-17-12-30(13-18-32)26-35-23-22-29-8-4-3-5-9-29/h3-5,8-9,12-15,17-20,28,35H,6-7,10-11,16,21-27H2,1-2H3; Key:SEQAMPXQRKYYQF-UHFFFAOYSA-N;
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Short description: Chemical compound

SB-699551 is a drug which was the first compound developed to act as a selective antagonist for the serotonin receptor 5-HT_5A, with selectivity of around 100x over other serotonin receptor subtypes.^[1] Multiple therapeutic roles have been suggested for 5-HT_5A ligands due to the presence of this receptor in several areas of the brain, but research is still at an early stage,^[2] In animal studies, SB-699551 was found to block cue-mediated responding to LSD, again suggesting an antipsychotic type of activity.^[3] It also reduces the viability of certain types of cancer cells in vitro, suggesting the 5-HT_5A receptor as a possible target for novel chemotherapy drugs.^[4]^[5]

References

↑ "SB-699551-A (3-cyclopentyl-N-[2-(dimethylamino)ethyl]-N-[(4'-{[(2-phenylethyl)amino]methyl}-4-biphenylyl)methyl]propanamide dihydrochloride), a novel 5-ht5A receptor-selective antagonist, enhances 5-HT neuronal function: Evidence for an autoreceptor role for the 5-ht5A receptor in guinea pig brain". Neuropharmacology 51 (3): 566–577. September 2006. doi:10.1016/j.neuropharm.2006.04.019. PMID 16846620.
↑ "The effects of a 5-HT5A receptor antagonist in a ketamine-based rat model of cognitive dysfunction and the negative symptoms of schizophrenia". Neuropharmacology 105: 351–360. June 2016. doi:10.1016/j.neuropharm.2016.01.035. PMID 26826431.
↑ "Serotonin type 5A receptor antagonists inhibit D-lysergic acid diethylamide discriminatory cue in rats". Journal of Psychopharmacology 33 (11): 1447–1455. November 2019. doi:10.1177/0269881119867603. PMID 31452444.
↑ "High-throughput screen identifies 5-HT receptor as a modulator of AR and a therapeutic target for prostate cancer". The Prostate 80 (11): 885–894. August 2020. doi:10.1002/pros.24022. PMID 32483877.
↑ "Antagonists of the serotonin receptor 5A target human breast tumor initiating cells". BMC Cancer 20 (1): 724. August 2020. doi:10.1186/s12885-020-07193-6. PMID 32758183.

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Original source: https://en.wikipedia.org/wiki/SB-699551. Read more

[1] "SB-699551-A (3-cyclopentyl-N-[2-(dimethylamino)ethyl]-N-[(4'-{[(2-phenylethyl)amino]methyl}-4-biphenylyl)methyl]propanamide dihydrochloride), a novel 5-ht5A receptor-selective antagonist, enhances 5-HT neuronal function: Evidence for an autoreceptor role for the 5-ht5A receptor in guinea pig brain". Neuropharmacology 51 (3): 566–577. September 2006. doi:10.1016/j.neuropharm.2006.04.019. PMID 16846620.

[2] "The effects of a 5-HT5A receptor antagonist in a ketamine-based rat model of cognitive dysfunction and the negative symptoms of schizophrenia". Neuropharmacology 105: 351–360. June 2016. doi:10.1016/j.neuropharm.2016.01.035. PMID 26826431.

[3] "Serotonin type 5A receptor antagonists inhibit D-lysergic acid diethylamide discriminatory cue in rats". Journal of Psychopharmacology 33 (11): 1447–1455. November 2019. doi:10.1177/0269881119867603. PMID 31452444.

[pmid32483877-4] "High-throughput screen identifies 5-HT receptor as a modulator of AR and a therapeutic target for prostate cancer". The Prostate 80 (11): 885–894. August 2020. doi:10.1002/pros.24022. PMID 32483877.

[pmid32758183-5] "Antagonists of the serotonin receptor 5A target human breast tumor initiating cells". BMC Cancer 20 (1): 724. August 2020. doi:10.1186/s12885-020-07193-6. PMID 32758183.

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Identifiers

IUPAC name 3-cyclopentyl-N-[2-(dimethylamino)ethyl]-N-[(4'-([(2-phenylethyl)amino]methyl)-4-biphenylyl)methyl]propanamide
CAS Number	791789-61-2^Y
PubChem CID	11168182
ChemSpider	9343277
UNII	3FN59X9DPR
Chemical and physical data
Formula	C₃₄H₄₅N₃O
Molar mass	511.754 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C2CCCC2CCC(=O)N(CCN(C)C)Cc(cc3)ccc3-c(cc1)ccc1CNCCc4ccccc4
InChI InChI=1S/C34H45N3O/c1-36(2)24-25-37(34(38)21-16-28-10-6-7-11-28)27-31-14-19-33(20-15-31)32-17-12-30(13-18-32)26-35-23-22-29-8-4-3-5-9-29/h3-5,8-9,12-15,17-20,28,35H,6-7,10-11,16,21-27H2,1-2H3 Key:SEQAMPXQRKYYQF-UHFFFAOYSA-N
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