e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthetic, biocatalytic acetylation and antituberculosis activity evaluation studies on (+/-)-4-alkyl-3, 4-dihydro-3-omega-hydroxyalkyl-2H-1, 3-benzoxazines

…, A Dhawan, NK Sharma, V Kumar, S Kumar…

Index: Shakil, Najam A.; Dhawan, Ashish; Sharma, Nawal K.; Kumar, Vijayendra; Kumar, Sujeet; Bose, Mridula; Raj, Hanumantharao G.; Olsen, Carl E.; Cholli, Ashok L.; Samuelson, Lynne A.; Kumar, Jayant; Watterson, Arthur C.; Parmar, Virinder S.; Prasad, Ashok K. Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003 , vol. 42, # 8 p. 1958 - 1969

Full Text: HTML

Citation Number: 16

Abstract

Abstract: Five novel (±)-4-alkyl-3, 4-dihydro-3-ω-hydroxyalkyl-2H-1, 3-benzoxazines have been synthesized by Mannich-type condensation of N-ω-hydroxyalkyl, N-[1-(2- hydroxypheny l) ethyl/propyl] amine and formaldehyde in 55 to 60% yields. Porcine pancreatic lipase in tetrahydrofuran catalyses the acetylation of these benzoxazines in an enantioselective fashion. This perhaps is the first report of the resolution of benzoxazines ...

Formaldehyde Structure

2-[1-(5-hydroxypentylamino)ethyl]phenol Structure

2-[1-(5-hydroxy...

~53%

5-(4-methyl-2,4-dihydro-1,3-benzoxazin-3-yl)pentan-1-ol Structure

5-(4-methyl-2,4...

5-Aminopentanol Structure

5-Aminopentanol

~%

5-(4-methyl-2,4-dihydro-1,3-benzoxazin-3-yl)pentan-1-ol Structure

5-(4-methyl-2,4...

Ortho-Hydroxyacetophenone Structure

Ortho-Hydroxyac...

~%

5-(4-methyl-2,4-dihydro-1,3-benzoxazin-3-yl)pentan-1-ol Structure

5-(4-methyl-2,4...

6-[1-(5-hydroxypentylamino)ethylidene]cyclohexa-2,4-dien-1-one Structure

6-[1-(5-hydroxy...

~%

5-(4-methyl-2,4-dihydro-1,3-benzoxazin-3-yl)pentan-1-ol Structure

5-(4-methyl-2,4...

Formaldehyde Structure

2-[1-(3-hydroxypropylamino)propyl]phenol Structure

2-[1-(3-hydroxy...

~54%

2H-1,3-Benzoxazine-3(4H)-propanol,4-ethyl-(9CI) Structure

2H-1,3-Benzoxaz...

2-Propionylphenol Structure

2-Propionylphenol

~%

2H-1,3-Benzoxazine-3(4H)-propanol,4-ethyl-(9CI) Structure

2H-1,3-Benzoxaz...

6-[1-(3-hydroxypropylamino)propylidene]cyclohexa-2,4-dien-1-one Structure

6-[1-(3-hydroxy...

~%

2H-1,3-Benzoxazine-3(4H)-propanol,4-ethyl-(9CI) Structure

2H-1,3-Benzoxaz...

Formaldehyde Structure

2-[1-(5-hydroxypentylamino)propyl]phenol Structure

2-[1-(5-hydroxy...

~59%

5-(4-ethyl-2,4-dihydro-1,3-benzoxazin-3-yl)pentan-1-ol Structure

5-(4-ethyl-2,4-...

5-Aminopentanol Structure

5-Aminopentanol

~%

5-(4-ethyl-2,4-dihydro-1,3-benzoxazin-3-yl)pentan-1-ol Structure

5-(4-ethyl-2,4-...

2-Propionylphenol Structure

2-Propionylphenol

~%

5-(4-ethyl-2,4-dihydro-1,3-benzoxazin-3-yl)pentan-1-ol Structure

5-(4-ethyl-2,4-...

6-[1-(5-hydroxypentylamino)propylidene]cyclohexa-2,4-dien-1-one Structure

6-[1-(5-hydroxy...

~%

5-(4-ethyl-2,4-dihydro-1,3-benzoxazin-3-yl)pentan-1-ol Structure

5-(4-ethyl-2,4-...

6-[1-(2-hydroxyethylamino)ethylidene]cyclohexa-2,4-dien-1-one Structure

6-[1-(2-hydroxy...

~70%

2-[1-(2-HYDROXY-ETHYLAMINO)-ETHYL]-PHENOL Structure

2-[1-(2-HYDROXY...

Ortho-Hydroxyacetophenone Structure

Ortho-Hydroxyac...

~%

2-[1-(2-HYDROXY-ETHYLAMINO)-ETHYL]-PHENOL Structure

2-[1-(2-HYDROXY...

5-Aminopentanol Structure

5-Aminopentanol

Ortho-Hydroxyacetophenone Structure

Ortho-Hydroxyac...

~78%

6-[1-(5-hydroxypentylamino)ethylidene]cyclohexa-2,4-dien-1-one Structure

6-[1-(5-hydroxy...

2-Propionylphenol Structure

2-Propionylphenol

3-Aminopropan-1-ol Structure

3-Aminopropan-1-ol

~90%

6-[1-(3-hydroxypropylamino)propylidene]cyclohexa-2,4-dien-1-one Structure

6-[1-(3-hydroxy...

5-Aminopentanol Structure

5-Aminopentanol

2-Propionylphenol Structure

2-Propionylphenol

~77%

6-[1-(5-hydroxypentylamino)propylidene]cyclohexa-2,4-dien-1-one Structure

6-[1-(5-hydroxy...

6-[1-(5-hydroxypentylamino)ethylidene]cyclohexa-2,4-dien-1-one Structure

6-[1-(5-hydroxy...

~66%

2-[1-(5-hydroxypentylamino)ethyl]phenol Structure

2-[1-(5-hydroxy...

5-Aminopentanol Structure

5-Aminopentanol

~%

2-[1-(5-hydroxypentylamino)ethyl]phenol Structure

2-[1-(5-hydroxy...

Ortho-Hydroxyacetophenone Structure

Ortho-Hydroxyac...

~%

2-[1-(5-hydroxypentylamino)ethyl]phenol Structure

2-[1-(5-hydroxy...

6-[1-(3-hydroxypropylamino)propylidene]cyclohexa-2,4-dien-1-one Structure

6-[1-(3-hydroxy...

~50%

2-[1-(3-hydroxypropylamino)propyl]phenol Structure

2-[1-(3-hydroxy...

2-Propionylphenol Structure

2-Propionylphenol

~%

2-[1-(3-hydroxypropylamino)propyl]phenol Structure

2-[1-(3-hydroxy...

6-[1-(5-hydroxypentylamino)propylidene]cyclohexa-2,4-dien-1-one Structure

6-[1-(5-hydroxy...

~54%

2-[1-(5-hydroxypentylamino)propyl]phenol Structure

2-[1-(5-hydroxy...

5-Aminopentanol Structure

5-Aminopentanol

~%

2-[1-(5-hydroxypentylamino)propyl]phenol Structure

2-[1-(5-hydroxy...

2-Propionylphenol Structure

2-Propionylphenol

~%

2-[1-(5-hydroxypentylamino)propyl]phenol Structure

2-[1-(5-hydroxy...