L-765,314

L-765,314
Identifiers
	IUPAC name benzyl (2S)-4-(4-amino-6,7-dimethoxyquinazolin-2-yl)-2-(tert-butylcarbamoyl)piperazine-1-carboxylate;
CAS Number	189349-50-6 ;
PubChem CID	6603904;
IUPHAR/BPS	506;
ChemSpider	5036212 ;
UNII	CR7JLF2GBM;
ChEMBL	ChEMBL19476 ;
CompTox Dashboard (EPA)	DTXSID901028767 ;
Chemical and physical data
Formula	C27H34N6O5
Molar mass	522.606 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)(C)NC(=O)[C@@H]1CN(CCN1C(=O)OCc2ccccc2)c3nc4cc(c(cc4c(n3)N)OC)OC;
	InChI InChI=1S/C27H34N6O5/c1-27(2,3)31-24(34)20-15-32(11-12-33(20)26(35)38-16-17-9-7-6-8-10-17)25-29-19-14-22(37-5)21(36-4)13-18(19)23(28)30-25/h6-10,13-14,20H,11-12,15-16H2,1-5H3,(H,31,34)(H2,28,29,30)/t20-/m0/s1 ; Key:CGWOIDCAGBKOQL-FQEVSTJZSA-N ;
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L-765,314 is a drug which acts as a potent and selective antagonist of the α₁-adrenergic receptor subtype α_1B.^[1] It has mainly been used to investigate the role of α_1B-adrenergic receptors in the regulation of blood pressure.^[2]^[3] The α_1B receptor is also thought to have an important role in the brain; however, L-765,314 does not cross the blood–brain barrier.^[4]

References

^ Patane MA, Scott AL, Broten TP, Chang RS, Ransom RW, DiSalvo J, Forray C, Bock MG (April 1998). "4-Amino-2-[4-[1-(benzyloxycarbonyl)-2(S)- [[(1,1-dimethylethyl)amino]carbonyl]-piperazinyl]-6, 7-dimethoxyquinazoline (L-765,314): a potent and selective alpha1b adrenergic receptor antagonist ". Journal of Medicinal Chemistry. 41 (8): 1205–8. doi:10.1021/jm980053f. PMID 9548811.
^ Yang XP, Chiba S (August 2002). "Effects of L-765,314, a selective and potent alpha 1B-adrenoceptor antagonist, on periarterial nerve electrical stimulation-induced double-peaked constrictor responses in isolated dog splenic arteries". Japanese Journal of Pharmacology. 89 (4): 429–32. doi:10.1254/jjp.89.429. PMID 12233824.
^ Görnemann T, Villalón CM, Centurión D, Pertz HH (June 2009). "Phenylephrine contracts porcine pulmonary veins via alpha(1B)-, alpha(1D)-, and alpha(2)-adrenoceptors". European Journal of Pharmacology. 613 (1–3): 86–92. doi:10.1016/j.ejphar.2009.04.011. PMID 19376108.
^ Hillman KL, Doze VA, Porter JE (June 2007). "Alpha1A-adrenergic receptors are functionally expressed by a subpopulation of cornu ammonis 1 interneurons in rat hippocampus". The Journal of Pharmacology and Experimental Therapeutics. 321 (3): 1062–8. doi:10.1124/jpet.106.119297. PMID 17337632. S2CID 8780600.

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[pmid9548811-1] Patane MA, Scott AL, Broten TP, Chang RS, Ransom RW, DiSalvo J, Forray C, Bock MG (April 1998). "4-Amino-2-[4-[1-(benzyloxycarbonyl)-2(S)- [[(1,1-dimethylethyl)amino]carbonyl]-piperazinyl]-6, 7-dimethoxyquinazoline (L-765,314): a potent and selective alpha1b adrenergic receptor antagonist ". Journal of Medicinal Chemistry. 41 (8): 1205–8. doi:10.1021/jm980053f. PMID 9548811.

[pmid12233824-2] Yang XP, Chiba S (August 2002). "Effects of L-765,314, a selective and potent alpha 1B-adrenoceptor antagonist, on periarterial nerve electrical stimulation-induced double-peaked constrictor responses in isolated dog splenic arteries". Japanese Journal of Pharmacology. 89 (4): 429–32. doi:10.1254/jjp.89.429. PMID 12233824.

[pmid19376108-3] Görnemann T, Villalón CM, Centurión D, Pertz HH (June 2009). "Phenylephrine contracts porcine pulmonary veins via alpha(1B)-, alpha(1D)-, and alpha(2)-adrenoceptors". European Journal of Pharmacology. 613 (1–3): 86–92. doi:10.1016/j.ejphar.2009.04.011. PMID 19376108.

[pmid17337632-4] Hillman KL, Doze VA, Porter JE (June 2007). "Alpha1A-adrenergic receptors are functionally expressed by a subpopulation of cornu ammonis 1 interneurons in rat hippocampus". The Journal of Pharmacology and Experimental Therapeutics. 321 (3): 1062–8. doi:10.1124/jpet.106.119297. PMID 17337632. S2CID 8780600.

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Identifiers

IUPAC name benzyl (2S)-4-(4-amino-6,7-dimethoxyquinazolin-2-yl)-2-(tert-butylcarbamoyl)piperazine-1-carboxylate
CAS Number	189349-50-6^Y
PubChem CID	6603904
IUPHAR/BPS	506
ChemSpider	5036212^N
UNII	CR7JLF2GBM
ChEMBL	ChEMBL19476^N
CompTox Dashboard (EPA)	DTXSID901028767
Chemical and physical data
Formula	C₂₇H₃₄N₆O₅
Molar mass	522.606 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C)(C)NC(=O)[C@@H]1CN(CCN1C(=O)OCc2ccccc2)c3nc4cc(c(cc4c(n3)N)OC)OC
InChI InChI=1S/C27H34N6O5/c1-27(2,3)31-24(34)20-15-32(11-12-33(20)26(35)38-16-17-9-7-6-8-10-17)25-29-19-14-22(37-5)21(36-4)13-18(19)23(28)30-25/h6-10,13-14,20H,11-12,15-16H2,1-5H3,(H,31,34)(H2,28,29,30)/t20-/m0/s1^N Key:CGWOIDCAGBKOQL-FQEVSTJZSA-N^N
^NY (what is this?) (verify)