Jamal Mustafa

Synthesis and characterization of novel PUFA esters exhibiting potential anticancer activities: An in vitro study

Polyunsaturated fatty acids (PUFAs) have been reported to play a regulatory role in tumour growth progression. In the present study, we have synthesized ester derivatives of two important PUFA viz., linoleic acid (LA) and arachidonic acid (AA) with propofol, a widely used general anaesthetic-sedative agent. The novel propofol ester analogues have been found to inhibit various cancer cell lines in a dose-dependent manner. Moreover, the compounds have been found to induce apoptotic cell death by enhancing the release of cytochrome c and expression of caspase-3. The data of the present study suggest that novel propofol-PUFA esters have strong potential to emerge as effective anticancer agents.

Synthesis and Characterization of Novel n-9 Fatty Acid Conjugates Possessing Antineoplastic Properties

The present study enumerates the synthesis, spectroscopic characterization, and evaluation of anticancer potential of esters of two n-9 fatty acids viz., oleic acid (OLA) and ricinoleic acid (RCA) with 2,4- or 2,6-diisopropylphenol. The synthesis strategy involved esterification of the hydroxyl group of diisopropylphenol (propofol) to the terminal carboxyl group of n-9 fatty acid. The synthesized propofol-n-9 conjugates having greater lipophilic character were tested initially for cytotoxicity in-vitro. The conjugates showed specific growth inhibition of cancer cell lines whereas no effect was observed in normal cells. In general, pronounced growth inhibition was found against the human skin malignant melanoma cell line (SK-MEL-1). The anticancer potential was also determined by testing the effect of these conjugates on cell migration, cell adhesion and induction of apoptosis in SK-MEL-1 cancer cells. Propofol-OLA conjugates significantly induced apoptosis in contrast to propofol-RCA conjugates which showed only weak signals for cytochrome c. Conclusively, the synthesized novel ester conjugates showed considerable moderation of anti-tumor activity. This preliminary study places in-house synthesized conjugates into the new class of anticancer agents that possess selectivity toward cancer cells over normal cells.

Cyclopropenoid fatty acids ingnetum scandens and itsterculia pallens seed oils

Seed oils ofGnetum scandens (Gnetaceae) andSterculia pattens (Sterculiaceae) were found to contain sterculic (28.57,6.97) and malvalic (11.27,3.87) acids, respectively. Gas Chromatographic analysis of silver nitrate/meth-anol-treated methyl esters was used to establish the co-occurrence of these two acids.Sterculia foetida methyl esters were used as a reference standard.

Synthesis of sulfur heterocycles from α,β-unsaturated carbonyl fatty acid esters

Alkyl chain substituted oxathiolanes from allylic oxo are described. Reaction of methyl 4-oxo-trans-2-hexadecenoate (1) with β-mercaptoethanol yields methyl 4-oxathiolane-trans-2-hexadecenoate (II), methyl 4-oxathiolane-2(3)-(S-β-mercaptoethyl acetate) hexadecanoate (III) and methyl 4-oxathiolane-2(3)-(S-β-mercaptoethanol)hexadecanoate (IV).

Synthesis of tetrazole from α,β-unsaturated carbonyl fatty acid

Methyl 4-oxo-trans-2-octadecenoate (II), when treated with excess hydrazoic acid in the presence of BF3-etherate, produced 66% methyl 5-aza-nonadec-trans-2-enoate (4,5-d)-tetrazole (III), 10% methyl 5-aza-nonadec-4-oxo-trans-2-enoate (IV) and 7% pentadecamide (V). Individual products were characterized by spectral and elemental methods.

An 8-hydroxyoctadeca-cis-11,14-dienoic acid from Mirabilis jalapa seed oil

Abstract A fatty acid, found as a minor component in the seed oil of Mirabilis jalapa, is shown to be the hitherto unknown 8-hydroxyoctadeca-cis-11,14-dienoic acid.

Novel derivatives of methyl hexahydro-3-methyl-6-thioxo-1,2,4,5-tetrazine-3-nonanoate

Methyl hexahydro-3-methyl-6-thioxo-1,2,4,5-tetrazine-3-nonanoate (I) on treatment with reagents such as chloroacetic acid, 1,2-dibromoethane and 2-mercaptoethanol under different reaction conditions afforded methyl 3,4,6,7-tetrahydro-3-methyl-6-oxo-2H-thiazolo[3,2-b]-1,2,4,5-tetrazine-3-nonanoate (II), methyl 3,4,6,7-tetrahydro-3-methyl-2H-thiazolo[3,2-b]-1,2,4,5-tetrazine-3-nonanoate (III) and methyl 8-methyl-1-oxa-4-thia-6,7,9,10-tetraazaspiro-[4.5]-decane-8-nonanoate (IV) in good yields. The structures of compounds II–IV were established by elemental analysis, infrared (IR), nuclear magnetic resonance (NMR), and mass spectral data.

Derivatization of keto fatty acids: Part XIII—Synthesis of methyl hexahydro-3-alkyl-6-thioxo-1,2,4,5-tetrazine-3-alkanoates

Hexahydrothioxotetrazine fatty derivatives have been prepared by the reaction of thiocarbohydrazide with oxo fatty esters. Methyl 10-oxoundecanoate (I), methyl 9-oxooctadecanoate (II) and methyl 12-oxooctadecanoate (III) on treatment with thiocarbohydrazide furnish methyl hexahydro-3-methyl-6-thioxo-1,2,4,5-tetrazine-3-nonanoate (IV), methyl hexahydro-3-nonyl-6-thioxo-1,2,4,5-tetrazine-3-octanoate (V) and methyl hexahydro-3-hexyl-6-thioxo-1,2,4,5-tetrazine-3-undecanoate (VI), respectively, in fairly good yields. The structural assignments of the hexahydrothioxotetrazine fatty derivatives are based on microanalysis, infrared, nuclear magnetic resonance and mass spectrometry data.

Cupania anacardioides: A rich source of cyanolipids

Seed oil ofCupania anacardioides (Sapindaceae) was found to contain cyanolipid I and cyanolipid III at 41.3% and 11.7%, respectively. Structures of these cyanolipid fractions were confirmed by spectroscopic methods.

1,3-cycloaddition of nitrile oxide to olefinic fatty acid esters: synthesis of isoxazolines

Fatty acid isoxazolines were prepared as 1,3-cyclo adducts by the reaction of dipolar nitrile oxides and dipolarophilic olefinic fatty esters. The structures of the isoxazolines were established with the help of elemental analysis, infrared, nuclear magnetic resonance and mass spectrometry spectral data.