Regioselective Green Synthesis and Antimicrobial properties of full fused non mixed Heterocyclic Systems

One pot synthesis and reaction of triazinthione and triazinohydrazide derivatives with different electrophilic reagents in ordered to synthesis of some interesting non-mixed heterocyclic compounds. Structures of thiazolotriazine, triazolotriazine, pyrimidinyltriazine, and triazinotriazine derivatives were established via spectroscopic data and elemental analysis. The synthesized compounds were screened for their antimicrobial activity

Synthesis of Dynamic 2-Ethoxycarbonyl-4H-3, 1-Benzoxazin-4-one and its Behavior Towards Nitrogen Nucleophiles

The behavior of  2-ethoxycarbonyl-4H-3,1-benzoxazin-4-one and its behavior towards nitrogen nucleophiles namely, hydrazine hydrate, formamide, benzylamine, ethylamine, piperidine, ethanol amine, o-phenylenediamine, and glucosamine hydrochloride has been investigated. Also the reaction of 3-[aminoquinazolin-4(3H)-one-2-yl]formic acid hydrazide with aromatic aldehydes and phenylisothiocyanate has been discussed. The structure of the prepared compounds are elucidated using physical and spectral data like, FT-IR, 1HNMR, and mass spectroscopy

Effects of maternal hyperthermia on neurodevelopment: a literature review

Maternal hyperthermia, defined as a body temperature above 38°C (100.4°F) is due to various etiologies during pregnancy, and has been a subject of growing research interest. This phenomenon is considered a potential environmental teratogen contributing to the development of neural tube defects (NTDs) and other neurodevelopmental disorders. NTDs such as anencephaly and spina bifida, are known to be multifactorial in origin, resulting from a complex interplay between genetic and environmental factors. In this review, we aim to comprehensively analyze the effect of maternal hyperthermia on neurodevelopmental disorders and associated congenital anomalies. In addition, we will highlight both the infectious and noninfectious causes of maternal hyperthermia, as well as any risks and potential preventive measures. The literature search identified studies reporting associations between maternal hyperthermia and adverse fetal outcomes. We have evaluated the link between maternal fever due to infections during pregnancy and the increased likelihood of NTDs, particularly anencephaly and spina bifida, as well as Neurodevelopmental disorders. ​​In addition, the effects of non-infectious causes of maternal hyperthermia, including exercise and exposure to heat sources like saunas and hot tubs, on neurodevelopment have also been studied with varying degrees of evidence. Maternal hyperthermia elevates the risk of NTDs and neurodevelopmental disorders in infants, with folic acid offering partial protection, while other factors elevate this risk. However, further research is needed to define the precious association of these factors

Behaviour of 4-(4-acetoaminophenyl)-4-oxobut-2-enoic acid towards carbon and nitrogen nucleophiles and use of these products in the synthesis of some interesting heterocycles

The present work is devoted to study the interaction of-aroylacrylic acid derivative (1) with some containing active methylene compounds under Michael reaction conditions and afforded the Michael adducts (2a-e). When compound 1 was allowed to react with cyclohexanone in the presence of ammonium acetate as catalyst, it afforded hydroquinoline derivative (3). Interaction of the acid 1 with highly and moderately reactive hydrocarbons e.g. p-xylene and acetanilide in the presence of anhydrous aluminumchloride under Friedel-Crafts reaction conditions afforded (4a-b). On the other hand, when the acid 1 was allowed to react with benzyl amine in dry benzene yielded 2-benzylamino-4-(4-acetaminophenyl)-4-oxobutanoic acid (5). This later compound was used to synthesize some heterocyclic compounds (7-11). Also, aza Michael adduct (6) used asthe key starting material for the synthesis of some interesting heterocyclic compounds e.g. pyridazinone, oxazinoneand furanone derivatives (13-16)

Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis

A series of nine new 2,3-disubstituted 4(3H)-quinazolin-4-one derivatives was furnished starting from the 2-propyl-4(3H)-quinazoline-4-one (2). The reinvestigation of the key starting quinazolinone 2 was performed under microwave irradiation (MW) and solvent-free conditions. Combination of MW and phase-transfer catalysis using tetrabutylammonium benzoate (TBAB) as a novel neutral ionic catalyst was used for carrying out N-alkylation and condensation reactions of compound 2 as a simple, efficient and eco-friendly technique. The structure of the synthesized compounds was elucidated using different spectral and chemical analyses. In vitro antimicrobial activity of the compounds was investigated against four bacterial and two fungal strains; very modest activity was achieved. Some of the synthesized compounds were screened for their antitumor activity against different human tumor cell lines. The screened compounds exhibited a significant antitumor activity on some of the cancer cell lines, melanoma (SK-MEL-2), ovarian cancer (IGROV1), renal cancer (TK-10), prostate cancer (PC-3), breast cancer (MCF7) and colon cancer (HT29). The most active, even more active than the reference 5-fluorouracil, were found to be ethyl 4-[(4-oxo-2-propylquinazolin-3(4H)-yl)methyl]benzoate (3c), 3-{2-[6-(pyrrolidin-1-yl-sulfonyl)-1,2,3,4-tetrahydroquinoline]-2-oxoethyl}-2-propylquinazolin-4(3H)-one (3e), N’-[(E)-(2H-1,3-benzodioxo-5-yl)methylidene]-2-(4-oxo-2-propylquinazolin-3(4H)-yl)acetohydrazide (10a), N’-[(E)-(4-hydroxyphenyl)methylidene]-2-(4-oxo-2-propylquinazo-lin-3(4H)-yl)acetohydrazide (10b) and N’-[(E)-(4-nitrophenyl)methylidene]-2-(4-oxo-2-propylquinazolin-3(4H)-yl)acetohydrazide (10c)

Novel synthesis, ring transformation and anticancer activity of 1,3-thiazine, pyrimidine and triazolo[1,5-a]pyrimidine derivatives

Synthesis, heterocyclization and anticancer activity of a new series of heterocyclic compounds are described. Aminothiazine 1 was obtained from the base induced condensation of thiourea, benzaldehyde and ethyl cyanoacetate. The synthesis of N-phenyl amino pyrimidine derivative 2 was obtained as a result of reaction of aniline with compound 1. Compound 2 underwent ring opening and recyclization upon reaction with HCl or H2O2/ NaOH to afford the acid derivative 3 or oxazine 4, respectively. Thiazine 1 undergoes ring transformation upon the effect of NH2OH.HCl to produce pyrimidine derivative 5. Heterocyclization of compound 1 with thiosemicarbazide followed by oxidation with I2/AcOH afforded triazolopyrimidine 6 and 7, respectively. Alkylation of compound 1 was promoted by reaction of 1 with ethyl iodide to give alkylated thiazine 8 which in turn undergo ring transformation when subjected to reaction with hydrazine hydrate to give pyrazole derivative 9. Refluxing of amino-1,3-thiazine derivative 1 with ethyl bromoacetate in the presence of Et3N produce the alkylated pyrimidine product 10. Hydrazonolysis of 1,3-thiazine 1 with hydrazine or phenyhydrazine gave pyrimidine derivatives 11a,b, respectively. Compound 11b was cyclized with carbon disulfide or formaldehyde to produce triazolopyrimidines 12 and 13, respectively. Some of the new compounds were screened for anticancer activity and significant results were found for some compounds.               KEY WORDS: 1,3-Thiazine, Pyrimidine, Triazole, Pyrazole, Anticancer activity Bull. Chem. Soc. Ethiop. 2018, 32(3), 513-522.DOI: https://dx.doi.org/10.4314/bcse.v32i3.1

Ultrasonic and solvent free Synthesis of Regioselective Diastereomeric Adducts and Heterocyclic Products as antibacterial agent

Oxirane ring containing the carboxylic group in the α,β-position are useful intermediates in the synthesis of biologically active compounds. Epoxidation of 4-(4-acetylamino and/or bromophenyl)-4-oxo-but-2-enoic acids via ultrasound condition afforded α-oxirane carboxylic acid followed by regioselective diastereomeric adducts of camphor. The steric factor plays an important role in regioselectivity. Formation of oxirane and furan derivatives via ultrasonic condition was considered as key steps for synthesis of some important heterocyclic compounds. The structure of new synthesized compounds 2-9a,b were elucidated by elemental analysis and spectroscopic data. The antibacterial activity for the synthesized compounds was evaluated

Steric and Polar Factors Affecting Heteroring Opening of 2-[2-carboxy-3,4,5,6-tetrachloro]phenyl-4H-3,1-Benzoxazin-4-one by Nitrogen and Carbon Nucleophiles

The behavior of 2-[2-carboxy-3,4,5,6-tetrachloro]phenyl-4H-3,1-Benzoxazin-4-  one towards Nitrogen nucleophiles and Carbon nucleophiles under Friedel–Crafts' reaction conditions has been investigated and steric versus polar factors affecting ring opening has been studied

Utility of 4-(4-acetoaminophenyl)-4-oxo-but-2-enoic acid to prepare Pyranand Pyridine derivatives as building blocks in Heterocyclic Synthesis

The present work is devoted to study the interaction of β -aroylacrylic acid derivative (1) with malononitrile in the presence of piperidine and/or ammonium acetate, then using the formed compounds as a starting material for synthesizing fused and isolated heterocyclic system. Ithas been established that the β-aroylacrylic acid (1) reactwith malononitrile in (DMF) in the presence of piperidineas catalyst with formation of 4H-pyran derivative (2). Bychanging the catalyst into ammonium acetate, pyridine derivative (3) has been obtained. When compound (2) wasallowed to react with triethylorthoformate afforded ethoxymethyleneamino-4H-pyran (4). Compound (4) was used askey starting material for synthesizing some interesting annulated and heterocyclic systems (5-8). Also, the maleamic acid derivatives (9) and (15) have been synthesized via the interaction of (2) and (3) with maleic anhydride to study the behavior of the formed maleamic acid derivatives asanalogies of β-aroylacrylic towards different active methylene compounds under Michael addition reaction (10-14); (16-18)