Synthesis and biological study of medicinally important Mannich bases derived from 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a pentahydroxy naphthacene carboxamide

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 3, 2007, Pages 645-648

  Joshi, Sheela ^a   Manikpuri, Anju Das ^a   Tiwari, Prapti ^a  

^a DEVI AHILYA UNIVERSITY   (India)

Author keywords

4 (Dimethylamino) 1,4,4a,5,5a,6,11,12a octahydro 3,6,10,12,12a pentahydroxy naphthacene carboxamide; Antibacterial activity; Mannich bases; sulfonamides; Toxicity and statistical analysis

Indexed keywords

AMIDE; MANNICH BASE; NAPHTHACENE DERIVATIVE; SULFONAMIDE;

ARTICLE; CHEMICAL REACTION; DRUG ACTIVITY; GRAM NEGATIVE BACTERIUM; INFRARED RADIATION; LD 50; NONHUMAN; PATHOGENESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET RADIATION;

ANIMALS; ANTI-BACTERIAL AGENTS; INDICATORS AND REAGENTS; LETHAL DOSE 50; MAGNETIC RESONANCE SPECTROSCOPY; MANNICH BASES; MICE; NAPHTHACENES; PASTEURELLA MULTOCIDA; SALMONELLA ENTERITIDIS; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

NEGIBACTERIA;

EID: 33846290675     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.11.001     Document Type: Article

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21. General procedure for the preparation of Mannich base of 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a pentahydroxy naphthacene carboxamide-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,1 2a pentahydroxy naphthacene carboxamide (0.01 mol) was dissolved in 20 ml methanol. This was followed by equimolar addition of sulfonamide (0.01 mol) in small installments with constant stirring at efficient ice cooling. The reaction mixture was cooled well. Then 2.5 ml of formaldehyde solution (37%) was added slowly with continuous stirring. The mixture was kept as such for half an hour after adjusting the pH of reacting mixture to 3.5-4 with hydrochloric acid. After half an hour, the resulting reacting mixture was placed on a water bath for refluxing. The reflux time varied with different sulfonamides used. The mixture was then kept at 0 °C for 4 days, when the desired product formed. The Mannich base formed was recrystallized with dry distilled methanol/ethanol/DMF.
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