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US 2010/0016630 A1Published application
Antimicrobial derivatives of anacardic acid and process for preparing the same
AssigneeUnichem Laboratories Ltd
InventorsRadha Achanath, Malladi Srinivas, Candadal Seshadri Ramadoss
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Abstract
Derivatives of anacardic acid having antimicrobial properties and method for preparing said derivatives. The antimicrobial properties include bacteriostatic and bacteriocidal activity.
Claims10
Antimicrobial derivatives of anacardic acid of formula I
- wherein R1 comprises of H, CH3, C2H5, C3H7 or Ac;
- R2 is comprises of H, Br, F, Cl, I or NH2, NO2;
- R3 comprises of H, Br, F, Cl, I or NH2;
- NO2;
- R4 comprises of H, Br, or NO2;
- R5 comprises of H, NH2, OH. OCH3, OC2H5, OC3H7, OPh or NH—R7 or O—R7;
- and R7 comprises of a cyclic hydrocarbon or its derivatives including but not limited to:
- And R6 is an alkyl chain having a length of C1 to C20, the chain being either totally saturated or having one or more unsaturations.
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A process for preparing derivatives of anacardic acid comprising the steps of
- a. Preparing a mixture or suspension or solution of anacardic acid or its derivatives in any of the following:
- acetic anhydride, pyridine, acetyl chloride, H2SO4, HNO3, AcOH, AcOH/H2SO4, H2SO4/HNO3, DCM, alone or in combination,
- b. optionally adding bromine solution of bromine and DCM
- c. Stirring or incubating or refluxing the above at less than 5° C. to 50° C. for 10 minutes to 18 hours
- d. optionally acidifying the contents of step ‘c’
- e. pouring the contents of step ‘c’ or ‘d’ into water or ice-cold water or crushed ice to precipitate the anacardic acid derivative.
- F. optionally extracting the precipitated anacardic acid derivative of step ‘e’.
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A process for preparing derivatives of Anacardic acid comprising the steps of
- a. treating a solution of ancardic acid in acetone with anhydrous K2CO3, followed by dimethyl sulphate for 4 hours,
- b. evaporating the solvent to dryness under reduced pressure,
- c. dissolving residue in ethyl acetate and washing with water,
- d. evaporating solvent under reduced pressure,
- e. refluxing the product with mixture of KOH/BuOH/H2O for 2 hours,
- f. cooling the mixture to room temperature
- g. acidifying the reaction mixture with HCl
- h. separating organic layer and washing with water and
- i. evaporating the solvent under pressure to obtain crude product,
- j. optionally purifying the crude product by triturating with hexane to obtain a solid, filtering said solid, washing filtered solid with hexane followed by vacuum drying for 2 hrs.
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A process for preparing derivatives of Anacardic acid comprising the steps of
- a. treating a solution MAA in dichloromethane with thionylchloride for 1 hour or treating a solution MAA with bakuchiol in dichloromethane with DCC followed by DMAP for 2 hrs
- b. removing solvent under reduced pressure to obtain residue and optionally
- c. dissolving residue in dichloromethane
- d. adding dropwise to cold suspension at 10° C. of 6-APA or PABA or Phe or Tyr or PNA in DCM/TEA over a period of about 10 min
- e. stirring the mixture at room temperature for 90 min to 17 hours
- f. acidifying reaction mixture with citric acid or HCl
- g. separating the organic layer and washing it with water
- h. evaporating the solvent to dryness to get crude product
- i. optionally purifying the crude product
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Dependencies are inferred from the claim text.