Mohammad Ismail Hossain Chemical Engineering Department Universiti Teknologi PETRONAS (UTP) Bander Seri Iskandar, 31750, Tronoh, Perak, MALAYSIA.
Cell: +60103755854
------------------------------------------- Assistant Professor Department of Chemistry University of Chittagong,Chittagong 4331, BANGLADESH.
ismailcu@gmail.com
Mohammad Ismail Hossain assumed his current responsibilities as the Faculty of the Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong, Bangladesh in July 2004, first as ‘Lecturer’ and, since December 2006, as ‘Assistant Professor’. Prior to that, he worked as a faculty in Rangpur Cadet College, Rangpur.
Mr. Hossain commenced studying a Doctor of Engineering (D.Engn) in the Department of Chemical Engineering in Universiti Teknologi PETRONAS (UTP), Perak Darul Ridzuan, Malaysia from July 2009 as a Graduate Assistant (GA) with Dr. Mohanad M-A.A. El-Harbawi, His previous qualifications include two master degree: one Master of Philosophy (M.Phil.) and the other Masters of Science (M.Sc.) with major in Bioorganic Chemistry, and a Bachelor of Science (B.Sc.) with honours in Chemistry, all from the University of Chittagong, Bangladesh.
He has the honor to be selected as a fellow for Chinese Government Scholarship by China Scholarship Council (CSC), China (2009) and as an awardee of 2009 UNE International Stipend Scholarship from University of New England (UNE), Armidale, NSW, Australia.
Mr. Hossain's primary interest in the research is of toxicity and biodegradability study of Ionic Liquids on the fate of aquatic environment. He is also contributing in the research of Synthetic Organic Chemistry and Characterization of heterocyclic fused compounds with possibility to drug discovery.
He has authored a number of journal articles and attended to the conference’s in different countries.
Abstract: A series of choline carboxylate salts have been synthesized by neutralization of choline hydroxide solution with acetic, propanoic, butanoic, pivalic and hexanoic acids. The ionic liquids (ILs) so obtained were characterized by NMR spectroscopy, thermal methods and elemental analysis. Key physical properties (density, viscosity and refractive index) were measured for the propanoate, butanoate and hexanoate salts at temperatures (293.15 to 353.15) K. The densities were used to estimate molecular volumes, standard entropies, crystal lattice energies and thermal expansion coefficients of the three salts. All five choline carboxylates were found to have cytotoxicities (IC50 values) on the human breast cancer cell line, MCF-7 above 10 mM, indicating they are less toxic than common imidazolium-based ILs.
Abstract: Hydroxyl functionalized ionic liquids (HFILs), 1-(6-hydroxylhexyl)-3-alkylimidazolium chloride, [IMn6OH][Cl] (n=0, 1, 2, 4) have been synthesized from the precursor imidazole, methylimidazole, ethylimidazole and butylimidazole in our laboratory. Experimental density Ï, dynamic viscosity η, refractive index, nD and surface tension, ï³ were studied as a function of temperature in atmospheric pressure. Empirical correlations were established to explain the experimental results. Thermal expansion coefficient of these ionic liquids was calculated from the experimental densities. By increasing the carbon chain length of imidazolium cation decreases the density and surface tension, whereas it increases the viscosity and refractive index, which is consistent with other ionic liquids.
Abstract: Fused pyrimidines, 2,4,6,8-Tetrahydro-5-(4/-ethylphenyl)-10-aryl-2,4,6,8-tetraoxo-5H,10H-pyrido[2,3-d:6,5-d/]dipyrimidine [1-7], were prepared in good yield through a simple, clean and three-component one-pot cyclo-condensation reaction of barbituric acid, aromatic aldehydes and 4-ethylanilline under reflux in nitrogen atmosphere. The synthesized products were characterized with IR, NMR spectroscopy and CHNS analysis, which give good information about their confirmation of synthesis. All the compounds have been screened for their antimicrobial activity with four human pathogenic bacteria: Bacillus cereus BTCC 19, Salmonella typhi AE 14612, Shigella dysenteria AE 14396, Listeria monocytogenes and three phytopathogenic fungi: Macrophomina phaseolina (Tassi) Goid, Fusarium equiseti (Corda) Sacc, Colletotricum corchori Ikata (Yoshida) and Alternaria alternata (Fr.) Kedissler. The precursor barbituric acid was compared with the activity exhibited for the synthesized fused pyridopyridines, which show the increased inhibition against the bacterial growth after cyclization. Stability and aromaticity of heterocycles can be the cause for good inhibition of those prepared compounds.
Abstract: A series of chalcones (1-9) were prepared by Claisen-Schmidt condensation of methyl ketones with several aromatic
aldehydes in presence of aqueous solution of sodium hydroxide using microwave irradiations. The reaction is clean with
shorter reaction time, mild reaction condition, eco-friendly, excellent yield as compared to conventional methods and
reduces the use of volatile organic compounds (VOCs). Variety of functional groups such as nitro, chloro, amino and ether
survived under the reaction conditions. The structures of the novel synthesised chalcones have been established on the basis
of their IR, NMR spectral data and elemental analyses. These compounds were screened for their antibacterial activities
against five pathogenic organisms: Pseudomonas aeruginosa, Staphylococcus aureus (ATCC 6538), Vibrio choloriae,
Shigella dysenteriae (AE 14396) and Salmonella typhi (AE 14612 (Table.1) and antifungal activity against three organisms:
Aspargilllus flavus, Saccharomyces cerevisiae and Candida albicans (Table.2) using disc diffusion method and poisonedfood
technique respectively. Some of them were found to possess significant activity, when compared to standard drugs.
Abstract: Eight hydroxylammonium-based room temperature ionic liquids (ILs) have been synthesized by acid-base neutralization of ethanolamines with organic acids. The ILs were characterized by infrared and nuclear magnetic resonance spectroscopies and elemental analysis. Their anti-microbial activities were determined using the well-diffusion method. All eight ILs were toxic to Staphylococcus aureus, while 2-hydroxyethylammonium lactate and 2-hydroxy-N-(2-hydroxyethyl)-N-methylethanaminium acetate showed high anti-microbial activity against a wide range of human pathogens.
Abstract: Acridine-1,8-dione [1-8], were prepared in good yield through a simple, clean and three-component one-pot cyclo-condensation reaction of dimedone, aromatic aldehydes and 4-ethylanilline under reflux in nitrogen atmosphere. The synthesized products were characterized with IR, NMR spectroscopy and CHNS analysis, which give good information about their confirmation of synthesis. All the compounds have been screened for their antimicrobial activity with four human pathogenic bacteria: Bacillus cereus BTCC 19, Salmonella typhi AE 14612, Shigella dysenteria AE 14396, Listeria monocytogenes and four phytopathogenic fungi: Macrophomina phaseolina (Tassi) Goid, Fusarium equiseti (Corda) Sacc, Colletotricum corchori Ikata (Yoshida) and Alternaria alternata (Fr.) Kedissler. The precursor dimedone was compared with the activity exhibited for the synthesized fused pyridopyridines, which show the increased inhibition against the bacterial growth after cyclization. Stability and aromaticity of heterocycles can be the cause for good inhibition of those prepared compounds.
Abstract: A new model has been developed that expresses the toxicity of a wide variety of ionic liquids (ILs) towards the freshwater flea Daphnia magna to published toxicity data (EC50 values) by means of quantitative structure-activity relationship (QSAR). The data were analyzed using summed contributions from the cations, and their alkyl substituents, and anions. The model was developed via Multiple Linear Regression (MLR) Analysis and polynomial model using MATLAB. The developed model is capable of reliably predicting IL toxicities towards D. magna with high accuracy corresponding to R2 = 0.974 and standard error of estimate of 0.028. This new model affords a practical, cost-effective and convenient alternative to experimental ecotoxicological assessment of many ILs.
Abstract: Fused pyrimidines, 8,9-dimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 5, 3,8,9-
trimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 6, 4-benzylidinehydrazono-5,6
dimethylthieno[2,3-d]pyrimidine 7, 4-[4/
-hydroxybenzylidine]hydrazono-5,6-dimethylthi-
eno[2,3-d]pyrimidine 8, 4-[4/
-tolylidin]hydrazono-5,6-dimethylthieno[2,3-d]pyrimidine 9,
4-[4/
-nitrobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 10 and 4-[4/
-
chlorobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 11 are prepared in
good yield by an initial treatment of 2-amino-4,5-dimethylthiophene-3-carbonitrile 1 with
formic acid, affording 5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one 2, which is
chlorinated with thionyl chloride and then hydrazinated with hydrazine hydrate. Finally
hydrazino compound 4 is reacted with formic acid, acetic anhydrate, benzaldehyde, p-
hydroxybenzaldehyde, p-toluayldehyde, p-nitrobenzaldehyde and p-chlorobenzaldehyde to
give thienotriazolopyrimidines 5-6 and thienopyrimidines 7-11 respectively. All the
compounds have been screened for their antimicrobial activity.
Abstract: Reaction of heteroaromatic o-aminonitrile with ethyl N-[bis(methylthio)methylene]amino acetate resulted in annelation of a thieno[3,2-e]imidazo[1,2-c]pyrimidine moiety in a one step process. [1,2,4]Triazolo[4,3-c]thieno[3,2-e]pyrimidine derivatives were prepared by initial treatment of o-aminonitrile with carbon disulfide, followed by methylation with methyl iodide and subsequent reaction with benzhydrazide and thiosemicarbazide, respectively. Hydrazinothieno[2,3-d]pyrimidine was prepared by cyclization of heteroaromatic o-aminoester with formamide, followed by chlorination and subsequent displacement with hydrazine. Treatment of the hydrazine derivative with acetylacetone, benzaldehyde and acetic anhydride afforded pyrazolylpyrimidine, benzylidenehydrazonopyrimidine and trizolopyrimidine derivatives, respectively. Some of these derivatives exhibited pronounced antimicrobial activity.
Abstract: Fused pyrimidines, 3-methyl-8, 9-diphenylfuro[3, 2-e][1,2,4]triazolo[4,3-c] pyrimidine (5) and
4-(3, 5-dimethylpyrazolyl)-5, 6-diphenylfuro[2, 3-d] pyrimidine (6) were prepared in good yields by an initial
treatment of o-aminoester (1) with formamide, affording 5, 6-diphenylfuro[2, 3-d]pyrimidin-4(3H)-one (2), which
is chlorinated with thionyl chloride and then hydrazinated with hydrazine hydrate. Finally, hydrazino compound
(4) was reacted with acetic anhydride and acetylacetone to give furopyrimidines (5) and (6) respectively.
Compound 2 also reacted with methanesulphonyl chloride and benzene sulphonyl chloride to give sulphonate
esters (7) and (8) respectively. Imidazopyrazolopyrimidine (12) was prepared from o-aminoester (11) and
annelating reagent (10). All the compounds were screened for their antibacterial and antifungal activity.
Abstract: 2-Amino-4,5-diphenylfuran-3-carbonitrile (2) reacted with N-bis(methylthio)methyleneglycine ethyl ester (1) to afford a double cyclized product 5-methylthio-8,9-diphenylfuro3,2-eimidazo1,2-cpyrimidin-2(3H)-one (3). Compound 2 also reacts with benzonitrile to give 4-amino-2,5,6-triphenylfuro2,3-dpyrimidine (4). Treatment of 2 with HCONH2, under reflux, afforded 4-amino-5,6-diphenylfuro2,3-dpyrimidine (5) which was then allowed to react with chloroacetaldehyde to give 8,9-diphenylfuro3,2-eimidazo1,2-cpyrimidine (6). Reaction of 2 with HCOOH gave 5,6-diphenylfuro2,3-dpyrimidin-4(3H)-one (7) which was then converted to its tosyl derivative (8). The antimicrobial activity of the synthesized compounds 2â8 was tested.
Abstract: In this study, two phosphonium based ionic liquids (butyl triphenyl phosphonium chloride and hexyl triphenylphosphonium bromide) have been synthesized using quarternisation process. The toxicities of these ionic liquids (ILs) are unknown and may be harmful to humans and the environment, therefore;the toxicity assessment of these ILs was carried out according to Organization for Economic Cooperation and Development (OECD) 203 guideline using female guppy fish (Poecilia reticulata). The median lethal concentrations (LC50) have been estimatedfor butyl triphenyl phosphonium chloride and for hexyl triphenyl phosphonium bromide to be 73.35 mg L-1 and 61.36 mgL-1 respectively. Both LC50 obtained can be identified as slightly toxic ionic liquids based on Acute Toxicity Rating Scale by Fish and Wildlife Service (FWS). On the other hand, no mortality of fish was recorded for octyltriphenylphosphonium chloride with highest concentration of 100 mgL-1. According to the rating scale, if no mortality was recorded after the fish exposed to concentration of 100 mgL-1and above, the ionic liquid is practically nontoxic.
Abstract: The acute toxicity of sixteen different ionic liquids (ILs) with imidazolium and ammonium cation was evaluated against freshwater organism: Guppy Fish, Poecillia reticulata. The LC50 were determined and found in the range 36.30-177.83 which lies on slightly toxic to practically nontoxic according to acute toxicity rating scale by Fish and Wildlife Service (FWS). Bis-(2-hydroxyethyl)-N-methylammonium formate (BHEMF) possess more toxic behavior than the other studied ILs. The result show the contribution of alkyl chain length likely to other toxicity studies. Imidazolium ILs exhibited less toxic behavior than the ammonium ILs. Incorporation of hydroxyl group in side chain of the imidazolium caion exhibited less toxic effect compare to the non-hydroxyl imidazolium ILs. The present study provides baseline information needed to assess the potential hazard that some ILs may pose and create detrimental effects to the aquatic bodies. It is not advisable to release them into freshwater ecosystems.
Abstract: Hydroxyl functionalized ionic liquids (HFILs), 1-(2-hydroxylethyl)-3-alkylimidazolium chloride, [IMn2OH][Cl] (n=0, 1, 4) have been synthesized from the precursor imidazole, methylimidazole and butylimidazole in our laboratory. The structures of the synthesized compounds were confirmed by IR, NMR spectroscopy and elemental analysis. Microbial screening was performed using Well-diffusion method to predict the concentration range where the EC50 can be found. Minimal Inhibitory Concentration can be tracked considering the transparent and opaque well concentration and EC50 was calculated from viability-dose curve. Five different bacteria were used to carry out these experiment, which were gram positive staphylococcus aureus and listeria monocytogenes, gram negative escherichia coli, aeromonas hydrophila and salmonella enterica. Serial dilution method was used to get the result with seven different concentrations: 250, 125, 62.5, 31.3, 15.6, 7.81, 3.91 mM. All four ionic liquids show the MIC result within 125 and 62.5 mM. EC50 values give a trend to decrease with increasing the alkyl chain length for Escherichia coli, where as staphylococcus aureus show opposite trends. All the result were compared with standard antibiotic Gentamycin, which show more toxic compare to the tested ionic liquids.
Abstract: Ionic liquids (ILs) are compounds of high interest for industry because of their attractive properties as solvents, but the water solubility of these compounds will be a concern for aquatic pollution and related risks. Possibility of having a large number of these types of chemicals through the combination of cations and anions, can lead to study on knowledge base database for toxicity prediction and estimate the toxicity from the structural contribution. A new model has been developed that expresses the toxicity of a wide variety of ILs towards the freshwater flea Daphnia magna (EC50 values) by means of quantitative structure-activity relationship (QSAR). The data were analyzed using summed contributions from the cations, and their alkyl substituents, and anions. The model was developed via Multiple Linear Regression (MLR) Analysis and polynomial model using MATLAB software. The developed model is capable of reliably predicting IL toxicities with high accuracy corresponding to R2 = 0.974 and standard error of estimate of 0.028. This new model affords a practical, cost-effective and convenient alternative to experimental ecotoxicological assessment of many ILs.
Abstract: The use of ionic liquids (ILs) as an environmentally friendly replacement for traditional organic solvents in industry is very promising. While ILs are relatively benign to the atmosphere because they are non-volatile, their impacts on aquatic organisms and communities have not been studied more. Some (eco)toxicological studies of ILs have been done so far with bacteria, phytoplankton, freshwater invertebrates and fishes and they showed that ILs are toxic to aquatic organisms ranging from bacteria to fish. Nonetheless, a detail study of those organisms is just as important if we are fully understood the prospective fate and effects of ILs in the aquatic environment. The effect of ILs on the environment may be approached performing specific tests in order to get direct information on ILs properties linked to the environment and estimating ecotoxicity, biodegradability and lipophilicity through structure activity relationship, or structure-property correlations of ILs. For aquatic toxicity, generally, bioluminescent rod-shaped photobacterium Vibrio fischeri, freshwater algae Oocystis submarina and Cyclotella meneghiniana, Selenastrum capricornutum, invertebrates Daphnia magna, aquatic fish Pimephales promelas, zebrafish Danio rerio, freshwater snail Physa acuta are used to overview the total fate on aquatic environment.
Abstract: Ammonium based Ionic Liquids (ILs) were synthesized from alkanolamine by simply acid base neutralization reaction. The synthesized compounds were tested to evaluate their antibacterial properties for the first time. Five microbial strains were used in the study: Staphylococcus aureus, Listeria monocytogenes and gram-negative Salmonella typhi, Vibrio cholerae and Klebsiella pneumonia. The antimicrobial efficiency was measured by bacterial growth inhibition expressed as minimal inhibitory concentration (MIC) values. Ionic Liquids (ILs) are shown to display antimicrobial activity with the activities being greatly affected by increasing alkyl chain lengths. Hydroxyl functionalized ammonium ionic liquids show less effect compare to the non-functionalised one. Increase of the substituents in ammonium based ionic liquids show high anti-microbial activities.
Abstract: Ionic liquids are compounds of high interest for industry because of their attractive properties as solvents, but the water solubility of these compounds may lead to aquatic pollution and related risks. Experimental toxicity evaluation (Daphnia magna EC50) is a measurement of aquatic toxicity but there are theoretically over 1 trillion ionic liquids, which makes it necessary to estimate their properties by means of quantitative structureâactivity relationships (QSARs). In this work, a novel QSAR based on multiple linear regression method is applied to estimate the ecotoxicity of ionic liquids. A data set of Daphnia magna EC50 was assembled to develop a novel group contribution method for estimating the EC50 of ionic liquids. The results illustrated that the data range covered for log EC50 values in between 2.07 and -4.33. From the results the contributions of anion, cation and alkyl substitutions has been established and found a good fitting value for predicting the EC50 by using SPSS software 11.5.
Abstract: Various fused pyrimidines posses different biological and pharmaceutical activities. In our present studies, for the synthesis of new fused heterocyclic parent systems as pyridopyrimidine, pyrimidopyrimidine, acridinedione, quinazolinone, we used barbituric acid, thiobarbituric acid, dimedone as the starting materials to reaction with different suitable aryl aldehydes and aromatic amines as p-toluidine, 4-ethyl aniline and in some cases, ammonium acetate and thiourea were used as the source of nitrogen compound that was described by M. Kidwai et. al. Besides, we have synthesized some fused thienopyrimidines from the starting material o-aminonitrile following the way as Badr et al.
To prepare pyridopyrimidines, in Scheme 01, 2,4,6,8-Tetrahydro-5-(4/-ethylphenyl)-10-aryl-2,4,6,8-tetraoxo-5H,10H-pyrido[2,3-d:6,5-d/]pyrimidines [1a-g] were prepared from barbituric acid, aromatic aldehyde and ethyl aniline in methanol. And in scheme 02, 2,4,6,8-Tetrahydro-5-tolyl-10-aryl-2,4,6,8-tetraoxo-5H,10H-pyrido[2,3-d:6,5-d/]pyrimidines [2a-e] were obtained from the reaction of barbituric acid, aromatic aldehyde and p-toluidine in methanol with reflux. But in scheme 03, 5-Aryl-2,4,6,8-tetrahydropyrimido[5/,4/:5,6]pyrido[2,3-d]pyrimidine-2,4,6,8-tetraones [3a-d] was prepared from barbituric acid, aromatic aldehyde and ammonium acetate in presence of acetic acid. Then, 5-Aryl-7-thioxo-5,6,7,8-tetrahydro-1H-pyrimido[4,5-d]pyrimidine-2,4-diones [4a-d] were synthesized in scheme 04 from barbituric acid, aldehydes and thiourea.
To prepare acridinone and quinazolinone, in scheme 05, 3,3,6,6-Tetramethyl-9-aryl-10-p-tolyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione [5a-d] were prepared from dimedone, aromatic aldehyde and p-toluidine mixture in methanol. In scheme 06, 10-(4-Ethyl-phenyl)-3,3,6,6-tetramethyl-9-aryl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-diones [6a-c] were synthesized from dimedone, aromatic aldehyde and 4-ethylaniline in methanol. 3,3,6,6-Tetramethyl-9-aryl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-diones [7a-d] were formed from dimedone, aryl aldehyde and ammonium acetate in presence of acetic acid in scheme 07. But in scheme 08, different new compounds, 7,7-Dimethyl-4-phenyl-2-thioxo-2,3,4,6,7,8-hexahydro-1H-quinazolin-5-ones [8a-d] were formulated from dimedone, aryl aldehyde and thiourea in presence of conc. Hydrochloric acid.
But, in scheme 09, we included the research work for the formation of theinopyrimidines [9a-g] from o-aminonitrile as starting materials. They were prepared in good yield by initial treatment of 2-amino-4,5-dimethylthiophene-3-carbonitrile 100 with formic acid, affording 5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one 101, which is chlorinated with thionyl chloride and then hydrazinated with hydrazine hydrate. Finally hydrazino compound 103 was reacted with formic acid, acetic anhydrate, benzaldehyde, p-hydroxybenzaldehyde, p-toluayldehyde, p-nitrobenzaldehyde and p-chlorobenzaldehyde to give thienotriazolopyrimidines 9a-b and thienopyrimidines 9c-g respectively.
Abstract: Fused pyrimidines, 8,9-dimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 5, 3,8,9-trimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 6, 4-benzylidinehydrazono-5,6-dimethylthieno[2,3-d]pyrimidine 7, 4-[4-hydroxybenzylidine]hydrazono-5,6-dimethylthieno[2,3-d]pyrimidine 8, 4-[4-tolylidin]hydrazono-5,6-dimethylthieno[2,3-d]pyrimidine 9, 4-[4-nitrobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 10 and 4-[4-chlorobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 11 were prepared in good yield by an initial treatment of 2-amino-4,5-dimethylthiophene-3-carbonitrile 1 with formic acid, affording 5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one 2, which is chlorinated with thionyl chloride and then hydrazinated with hydrazine hydrate. Finally hydrazino compound 4 was reacted with formic acid, acetic anhydrate, benzaldehyde, p-hydroxybenzaldehyde, p-tolyldehyde, p-nitrobenzaldehyde and p-chlorobenzaldehyde gives thieno triazolopyrimidines 5-6 and thienopyrimidines 7-11 respectively. All the compounds were screened for their antibacterial and antifungal activity.
