A modified synthesis of iodoazidoaryl prazosin.
The antihypertension agent iodoazidoaryl prazosin (IAAP) has been made using a convergent route involving addition of an acylated piperazine 7 to 2-chloroquinazoline 5. IAAP has been shown to function as a multidrug resistance (MDR) reversal agent and bind to P-glycoprotein, a transmembrane transport protein. A study is also reported involving palladium-catalyzed substitution with amine heterocycles. With N,N-bis(2,6-diisopropyl)dihydroimidazolium chloride (10) as the ligand (2 mol %) for palladium(II) acetate (2 mol %) in THF at room temperature, morpholine added to 5 in 81% yield.
Andrus
Merritt B
MB
Brigham Young University, Department of Chemistry and Biochemistry, C100 BNSN, Provo, Utah 84602-5700, USA. mbandrus@chem.byu.edu
Mettath
Sashikumar N
SN
Song
Chun
C
D020168:ATP Binding Cassette Transporter, Subfamily B, Member 1 / Q000037:antagonists & inhibitors; D000959:Antihypertensive Agents / Q000138:chemical synthesis*; D001386:Azides / Q000138:chemical synthesis*; D018432:Drug Resistance, Multiple; D000077489:Piperazine; D010879:Piperazines / Q000737:chemistry; D011224:Prazosin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D020168:ATP Binding Cassette Transporter, Subfamily B, Member 1; D000959:Antihypertensive Agents; D001386:Azides; D010879:Piperazines; D000077489:Piperazine; C041552:azidoprazosin; D011224:Prazosin