“Prenalterol”的意思、由来-开放百科全书

Prenalterol exhibits adrenergic agonist activity in spite of an interposed oxymethylene group. The stereospecific synthesis devised for this molecule relies on the fact that the side chain is very similar in oxidation state to that of a sugar.

Condensation of monobenzone (2) with the epoxide derived from α-D-glucofuranose^[4] affords the glycosylated derivative (3). Hydrolytic removal of the acetonide protecting groups^[5] followed by cleavage of the sugar with periodate gives aldehyde (4). This is reduced to the glycol by means of NaBH₄ and the terminal alcohol is converted to the mesylate (5). Displacement of the leaving group with isopropylamine followed by hydrogenolytic removal of the O-benzyl ether affords the β₁-adrenergic selective adrenergic agonist prenalterol (6).

Racemic

Prepns of the racemic mixture: {{Cite patent|NL|6409883}} corresp to H. Köppe et al., {{US patent|3637852}} (1965, 1972 both to Boehringer Ingelheim); {{Cite patent|NL|301580}} corresp to A. F. Crowther, L. H. Smith, {{US patent|3501769}} (1965, 1970 both to ICI);^[6]

See also

References

1. ^{{cite journal |vauthors=Hadfield SE, Slee SJ, Snow HM |title=The cardiovascular pharmacology of xamoterol, cicloprolol, prenalterol and pindolol in the anaesthetised dog |journal=Br J Clin Pharmacol |volume=28 Suppl 1 |issue= Suppl 1|pages=78S–81S |year=1989 |pmid=2572262 |pmc=1379883 |doi= 10.1111/j.1365-2125.1989.tb03580.x }}
2. ^K. A. Jaeggi, H. Schroeter, and F. Ostermayer, {{Cite patent|DE|2503968}}; Chem. Abstr. 84, 5322 (1976).
3. ^corresp to {{US patent|3978041}} and {{US patent|4049797}} (1975, 1976, 1977, all to Ciba-Geigy).
4. ^http://www.chemspider.com/Chemical-Structure.9312824.html
5. ^{{cite journal|pmid=20543896|pmc=2882309|year=2010|author1=Liu|first1=Z|title=Acetonide Protection of Dopamine for the Synthesis of Highly Pure N-docosahexaenoyldopamine|journal=Tetrahedron Letters|volume=51|issue=18|pages=2403–2405|last2=Hu|first2=B. H.|last3=Messersmith|first3=P. B.|doi=10.1016/j.tetlet.2010.02.089}}
6. ^{{cite journal|doi=10.1021/jm00304a018|pmid=5793156|title=.beta.-Adrenergic blocking agents. V. 1-Amino-3-(substituted phenoxy)-2-propanols|journal=Journal of Medicinal Chemistry|volume=12|issue=4|pages=638|year=1969|last1=Crowther|first1=Albert F.|last2=Gilman|first2=D. J.|last3=McLoughlin|first3=B. J.|last4=Smith|first4=Leslie Harold|last5=Turner|first5=R. W.|last6=Wood|first6=T. M.}}

词条	Prenalterol
释义	Synthesis Stereospecific Racemic Further reading See also References {{Drugbox \| Verifiedfields = changed \| verifiedrevid = 464213907 \| IUPAC_name = 4-{[(2S)-2-hydroxy-3-(isopropylamino)propyl]oxy}phenol \| image = Prenalterol.svg \| width = 250 \| tradename = \| pregnancy_category = \| legal_status = Rx-only \| routes_of_administration = Oral, IV \| bioavailability = \| metabolism = \| elimination_half-life = \| excretion = \| CAS_number_Ref = {{cascite\|changed\|??}} \| CAS_number = 57526-81-5 \| ATC_prefix = C01 \| ATC_suffix = CA13 \| PubChem = 42396 \| IUPHAR_ligand = 537 \| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}} \| ChemSpiderID = 38665 \| UNII_Ref = {{fdacite\|correct\|FDA}} \| UNII = M4G34404CX \| ChEMBL_Ref = {{ebicite\|correct\|EBI}} \| ChEMBL = 1160714 \| C=12 \| H=19 \| N=1 \| O=3 \| molecular_weight = 225.284 g/mol \| smiles = O(c1ccc(O)cc1)C[C@@H](O)CNC(C)C \| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}} \| StdInChI = 1S/C12H19NO3/c1-9(2)13-7-11(15)8-16-12-5-3-10(14)4-6-12/h3-6,9,11,13-15H,7-8H2,1-2H3/t11-/m0/s1 \| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}} \| StdInChIKey = ADUKCCWBEDSMEB-NSHDSACASA-N }}Prenalterol is a cardiac stimulant which acts as a β₁ adrenoreceptor agonist.^[1] Synthesis Stereospecific Prenalterol exhibits adrenergic agonist activity in spite of an interposed oxymethylene group. The stereospecific synthesis devised for this molecule relies on the fact that the side chain is very similar in oxidation state to that of a sugar. Condensation of monobenzone (2) with the epoxide derived from α-D-glucofuranose^[4] affords the glycosylated derivative (3). Hydrolytic removal of the acetonide protecting groups^[5] followed by cleavage of the sugar with periodate gives aldehyde (4). This is reduced to the glycol by means of NaBH₄ and the terminal alcohol is converted to the mesylate (5). Displacement of the leaving group with isopropylamine followed by hydrogenolytic removal of the O-benzyl ether affords the β₁-adrenergic selective adrenergic agonist prenalterol (6). Racemic Prepns of the racemic mixture: {{Cite patent\|NL\|6409883}} corresp to H. Köppe et al., {{US patent\|3637852}} (1965, 1972 both to Boehringer Ingelheim); {{Cite patent\|NL\|301580}} corresp to A. F. Crowther, L. H. Smith, {{US patent\|3501769}} (1965, 1970 both to ICI);^[6] Further reading {{cite journal\|doi=10.1111/joim.1982.211.issue-s659\|year=1982\|journal=Acta Medica Scandinavica\|volume=211}} See also Primidolol Xamoterol References 1. ^{{cite journal \|vauthors=Hadfield SE, Slee SJ, Snow HM \|title=The cardiovascular pharmacology of xamoterol, cicloprolol, prenalterol and pindolol in the anaesthetised dog \|journal=Br J Clin Pharmacol \|volume=28 Suppl 1 \|issue= Suppl 1\|pages=78S–81S \|year=1989 \|pmid=2572262 \|pmc=1379883 \|doi= 10.1111/j.1365-2125.1989.tb03580.x }} 2. ^K. A. Jaeggi, H. Schroeter, and F. Ostermayer, {{Cite patent\|DE\|2503968}}; Chem. Abstr. 84, 5322 (1976). 3. ^corresp to {{US patent\|3978041}} and {{US patent\|4049797}} (1975, 1976, 1977, all to Ciba-Geigy). 4. ^http://www.chemspider.com/Chemical-Structure.9312824.html 5. ^{{cite journal\|pmid=20543896\|pmc=2882309\|year=2010\|author1=Liu\|first1=Z\|title=Acetonide Protection of Dopamine for the Synthesis of Highly Pure N-docosahexaenoyldopamine\|journal=Tetrahedron Letters\|volume=51\|issue=18\|pages=2403–2405\|last2=Hu\|first2=B. H.\|last3=Messersmith\|first3=P. B.\|doi=10.1016/j.tetlet.2010.02.089}} 6. ^{{cite journal\|doi=10.1021/jm00304a018\|pmid=5793156\|title=.beta.-Adrenergic blocking agents. V. 1-Amino-3-(substituted phenoxy)-2-propanols\|journal=Journal of Medicinal Chemistry\|volume=12\|issue=4\|pages=638\|year=1969\|last1=Crowther\|first1=Albert F.\|last2=Gilman\|first2=D. J.\|last3=McLoughlin\|first3=B. J.\|last4=Smith\|first4=Leslie Harold\|last5=Turner\|first5=R. W.\|last6=Wood\|first6=T. M.}} {{Cardiac stimulants excluding cardiac glycosides}}{{Adrenergics}}{{cardiovascular-drug-stub}} 7 : Alcohols\|Amines\|Beta1-adrenergic agonists\|Cardiac stimulants\|Inotropic agents\|Phenol ethers\|Phenols
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Synthesis

Stereospecific

Racemic

Further reading

See also

References