Jalal A Zahra

• PhD in Chemistry
• Professor (Full) at University of Jordan

A new thieno[2,3-b][1,4]dithiine-1,1-dioxide was prepared via intramolecular cycloaddition reaction between methyl β-sulfonyl ester of thiophene and carbon disulfide (CS 2) or ethoxycabonyl isothiocyanate. A new compound methyl 2-((2,5-dichlorothiophen-3-yl)sulfonyl) acetate as methyl β-sulfonyl ester was prepared via interaction between methyl 2-b...

The reaction of N′’(aryl)benzothiohydrazides with 2-chloro-6-((substituted)amino)-3-nitro-4-oxo-4H-thieno[2,3-b]thiopyran-5-carboxylate (13-15) under basic conditions (NEt3) in acetonitrile proceeds via thiophene ring-opening processes and yields, upon addition of iodomethane, the respective 1,3,4-thiadiazoline-6-sulfanylthiopyran-4(1H)-one hybrids...

Abstract: Aims: This study aimed at the synthesis of several spiro[benzofuran-3,3'-pyrroles] derivatives by a three-component reaction conducted by mixing DMAD, N-bridgehead heterocycles, and benzofuran-2,3-diones in dichloromethane at room temperature for 24 h. Moreover, in vitro evaluation of their cytotoxicity affinities against FMS-like tyrosin...

Background A series of novel 2-(isoquinolin-1-yl)-spiro[oxindole-3,3′-pyrrolines] were synthesized by a one-pot three-component reaction involving dimethyl acetylenedicarboxylate, 3- phenylimidazo[5,1-a]isoquinoline and N-alkylisatins in chloroform at ∼60 °C for 24 h. Aims This study aimed at the synthesis of novel spirooxindole-3,3'-pyrrolines de...

FMS-like tyrosine kinase 3 (Flt3) is an oncogenic kinase implicated in leukemia, with its primary association being acute myeloid leukemia (AML). Flt3-specific inhibitors have demonstrated promising outcomes in disrupting AML progression. While isoindigo derivatives, e.g., meisoindigo, have proven effective against chronic myeloid leukemia, their s...

This study introduces a novel class of hybrid compounds, namely, benzothieno[3,2’-f][1,3]oxazepines and their isomeric 2-oxo-2H-spiro[benzothiophene-3,3’-pyrrolines]. The synthetic strategy employs a three-component reaction and 1,4-Dipolar cycloaddition, yielding spiro and oxazepine compounds. Structural elucidation via NMR and MS analyses is comp...

A set of cyclopenten-[g]annelated isoindigos (5a-g) has been prepared and tested for their in vitro anti-proliferative activities against MCF-7 and HL60 cells. Among, the N-1-methyl-5′-nitro derivative (5g) displayed the highest activity against HL60 cells (IC 50 = 67 nM) and acted as the most potent Flt3 inhibitor. Compounds 5d-g exhibited moderat...

A novel set of thiochromano[2,3-c]pyrrolidine-1,3-diones incorporating α-hydroxy esters and their acids at C-9 locus, is prepared via direct interaction involving benzo[b]thiofuran-2,3-dione, maleimides and alkanols / H2O at 90 °C. Structures of the new product were deduced from HRMS and NMR spectral data, and confirmed by single-crystal X-ray crys...

Background Hydrazonoyl chloride, accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carboxylate, undergoes a reaction with sec-cyclic amines to generate N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. Introduction A novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates (7a-h) incorporating N-pi...

A library of N-benzylpyridinium-based compounds, 7a-j and 8a-j, was designed and synthesised as potential acetylcholinesterase) AChE (inhibitors. An in vitro assay for the synthesised compounds showed that most compounds had significant AChE inhibitory activities at the nanomolar and submicromolar levels. The benzyl (8a) and fluoro (8b) derivatives...

A series of novel 2-(quinolin-2-yl)-spiro[oxindole-3,3′-pyrrolines] were synthesized by one-pot three-component reaction involving dimethyl acetylenedicarboxylate, 1-phenylimidazo[1,5-a]quinoline and N-alkylisatins in chloroform at ∼60 °C for 24 h. Structures of these new spiro derivatives were deduced from HRMS and NMR spectral data. A plausible m...

This study reports the synthesis of seven new 8-amino-7-(aryl/hetaryl)fluoroquinolones and their antibacterial activity against 10 bacteria associated with microbial infections and foodborne illnesses. These fluoroquinolones are prepared via the reactions of selected aryl(hetaryl)boronic acids with ethyl-7chloro-6-fluoro-8-nitroquinolone-3-carboxyl...

A selected set of new N1-(indan-5-yl)amidrazones 4a-p, encompassing piperazines or related amines, has been prepared via interaction of the hydrazonoyl chloride 3 (derived from 5-aminoindane) with the appropriate sec-cyclic amine in the presence of triethyl amine. Their suggested structures are supported by IR, 1H NMR, 13C NMR, high resolution MS (...

A Selected set of 2-(quinolin-2-yl)-1,3-oxazepino[7,6- b ]indoles 4a–d and dihydroacenaphtho[1,2- f ][1,3]oxazepine 5 have been prepared via 1,4-dipolar cycloaddition reaction involving 1-phenylimidazo[1,5- a ]quinoline, dimethyl acetylenedicarboxylate, and N -(substituted)isatins or acenaphthoquinone. Structures of the new heterocycles 4a–d and 5...

Background: A variety of synthetic amidrazones are endowed with antitumor activity. Examples include N1-(thien-3-yl)amidrazone-2-carboxylates that exhibit high potency against breast cancer (MCF-7) and leukemia (K562) cell lines. These results prompted us to design and examine a new set of isomeric N1-(thienyl)amidrazone. Methods: The synthesis of...

A selected set of N1-(4-chloro-9-ethylcarbazol-3-yl)amidrazones (7a–n) has been synthesized by reacting the respective hydrazonoyl chloride 5 derived from 3-amino-9-ethylcarbazole (3), with an appropriate sec-cyclic amine (6a–n) in ethanol in the presence of triethylamine. Unexpectedly, aromatic ring chlorination occurred at C-4 of 3 during its con...

Background: Oriented research towards discovery of new antimicrobial agents continues as several microbes develop resistance to currently approved drugs. A selected set of N1-(1-ethyl-4-oxoquinolin- 6-yl)amidrazone-3-carboxylates incorporating N-piperazines or related congeners have been synthesized via interaction of the particular hydrazonoyl chl...

A series of novel pyridine-annelated spirooxindole-3,20 -pyrrolidines was prepared via 1,3-cycloaddition reaction involving N-methylmaleimide as 1,3- dipolarophile and the appropriate azomethine ylide. The latter 1,3-dipolar species were generated in situ via decarboxylative condensation reaction of the particular aamino acid with pyridine-annelate...

The antileukemic potential of isoindigos make them desired candidates for understanding their mechanism of action. We have recently synthesized a novel group of pyridone-annelated isoindigos and identified the derivative 5'-Cl that is cytotoxic to various cancer cell lines. In the present study, we analyzed the effect of this compound on cell cycle...

Abstract Background/Aims: In our quest to develop an isoindigo with improved efficacy and bioavailability, we recently synthesized a series of novel substituted pyridone-annelated isoindigo and evaluated their antiproliferative effects. We identified the compound [(E)-1-(5'-Chloro-2'-oxoindolin-3'-ylidene)-6-ethyl-2,3,6,9-tetrahydro-2,9-dioxo-1H-p...

A series of 2-hetaryl-4-fluoro-9-cyclopropyl-6-oxo-1H-imidazo[4,5-h]quinoline-7-carboxylic esters (3a-f) and their corresponding acids 4a-f have been prepared via microwave-assisted cyclocondensation reaction with some hetarene carboxaldehydes. The structures for these new esters and acids are based on spectral (IR, MS, and NMR) data. The in vitro...

A selected set of substituted pyridone-annelated isoindigos 3a–f has been synthesized via interaction of 5- and 6-substituted oxindoles 2a–f with 6-ethyl-1,2,9-trioxopyrrolo[3,2-f]quinoline-8-carboxylic acid (1) in acetic acid at reflux. Among these isoindigos, the 5'-chloro and 5'-bromo derivatives 3b and 3d show strong and selective antiprolifera...

Cyclocondensation reaction of ethyl 7,8-diamino-1-cyclopropyl-6-fluoro-4- oxo-1,4-dihydroquinoline-3-carboxylate (2) or the -3-carboxylic acid 3 with sym-1,2- diketones produced the corresponding ethyl 2,3-disubstituted pyrido[2,3-f]quinoxaline-8-carboxylates (4a-h) or the -8-carboxylic acids 5a - h, respectively. The structures for these new heter...

New model 1,2,4-triazino[6,5-h]quinolines 8a - c are prepared by oxidative cyclization of the respective N-(quinolin-8-yl)amidrazone precursors 7a - c using copper(II) chloride. Interestingly, the cyclized products 8a - c were found to be arylated at N1 position. Analytical and spectral (MS, NMR) data of the title products are in compliance with th...

Ethyl 7,8-diamino-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (6) and its free acid 7 are prepared by chemical reduction of the respective 7-azido-8-nitroquinoline 5. Consecutive nucleophilic addition and cyclocondensation reactions of 6 with α-acetyl-N-arylhydrazonoyl chlorides 8a - c in ethanol and triethylamine are site-selec...

Abstract New 9-(alkyl/aryl)-4-fluoro-6-oxo[1,2,5]thiadiazolo[3,4-h]quinoline-5-carboxylic acids and their esters were designed and synthesized. A detailed discussion of the reactions utilized in the preparation of the intermediate and target compounds is reported. All the newly synthesized compounds were fully characterized using all the physico-ch...

Interaction of 6-amino-1-ethyl-4-oxoquinoline-3-carboxylic ester (7) with chloral hydrate and hydroxylamine hydrochloride gave the corresponding isonitroso-acetamido derivative 8 which, upon treatment with concentrated sulfuric acid, was converted regioselectively into 1,2,9-trioxopyrrolo[3,2-f]quinoline-8-carboxylic acid (3). This novel tricyclic...

Direct interaction of salicylaldehyde oxyanion with ethyl 7-chloro-8-nitro-4-oxoquinoline-3- carboxylate (2) delivered the respective 7-(2-formyl-phenoxy)-8-nitro-4-oxoquinoline-3-carboxylic ester 3. Reductive cyclization of 3 furnished the corresponding 4-oxo-[1,4]benzoxazepino[2,3- h]quinoline-3-carboxylic ester 5. Acid-catalyzed hydrolysis of th...

Interaction of deprotonated malonic esters with 7-chloro-8-nitro-4-oxoquinoline-3-carboxylate (1) gave the respective 7-[bis(alkoxycarbonyl)-methyl] derivatives (2, 3) which were converted into the corresponding 7-(carboxymethyl)-8-nitro-4-oxoquinoline-3-carboxylic acid (4). Reductive lactamization of the latter furnished the target tetrahydro-2,6-...

A simple and efficient synthesis of 6-fluoro-4-oxopyrido[2,3-a]carbazole-3-carboxylic acids (13a-e) and a structurally related 6-fluoro-4-oxothieno[2',3':4,5]pyrrolo[3,2-h]quinoline (13f) was achieved via Stille arylation of 7-chloro-6-fluoro-8-nitro-4-oxoquinoline-3-carboxylate and a subsequent microwave-assisted phosphite-mediated Cadogan reactio...

A convenient one-pot synthesis of 1-alkyl-7-chloro-6-flouro-3-nitro-1,4-dihydro-4-quinolones is described via nitro-decarboxylation of the respective 4-oxo-1,4-dihydroquinoline-3-carboxylic acid precursors. Reduction of the former 3-nitroquinolones delivered the corresponding 3-aminoquinolones, envisaged as valuable synthons in drug research.

We report on the synthesis and the antimicrobial activity of 9-cyclopropyl-4-fluoro-6-oxo[1,2,5]thiadiazolo[3,4-h]quinoline-5-carboxylic acid (16), representative of a new class of antibacterial agents structurally related to the clinically successful fluoroquinolones. The novel 6-fluoroquinolone (16) is herein prepared, in good yield, by thermal c...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A convenient one-pot synthesis of 1-alkyl-7-chloro-6-flouro-3-nitro-1,4-dihydro-4-quinolones is described via nitro-decarboxylation of the respective 4-oxo-1,4-dihydroquinoline-3-carboxylic acid precursors. Reduction of the former 3-nitroquinolones delivered the corresponding 3-aminoquinolones, envisaged as valuable synthons in drug research.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

In basic media, 2-aminobenzoic acids (5) react with 2-[N-(1-carboxyphenyl)]hydrazonoyl chlorides (6, 7) (precursors of the reactive nitrile imine 1,3-dipolar species) to afford good yields of the corresponding 2-[N′-(1-carboxyphenyl-2-amino)hydrazino]benzoic acids (8a-d, 9a). The latter acyclic adducts, in the presence of 1,1′-carbonyldiimidazole (...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Cyclocondensation reaction of ethyl 7,8-diamino-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate with 1-methylisatin produced a separable mixture of the corresponding indolo[3,2-b]- and [2,3-b]pyrido[2,3-f]quinoxaline-3-carboxylates, of which the latter isomer predominates. On the other hand, interaction with 1H-isatin or 5-chloroisa...

The asymmetric unit of the title compound, C8H6N2O4, contains one half-molecule; a twofold rotation axis bisects the molecule. The quinoxaline ring is planar, which can be attributed to electron delocalization. In the crystal structure, intermolecular O—H� � �O hydrogen bonds link the molecules into R2 2(10) motifs, leading to layers, which interac...

The asymmetric unit of the title compound, C8H6N2O4, contains one half-mol­ecule; a twofold rotation axis bisects the molecule. The quinoxaline ring is planar, which can be attributed to electron delocalization. In the crystal structure, inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into R2²(10) motifs, leading to layers, which inter­act...

AbstractA series of ethyl 2-(substituted)-9-cyclopropyl-4-fluoro-6-oxo-1H-imidazo[4,5-h]quinoline-7-carboxylates has been prepared from ethyl 7,8-diamino-1,4-dihydroquinoline-3-carboxylate via thermally induced reactions with model alkanoic acids or via microwave-assisted cyclocondensation with some arene carboxaldehydes. Acid-catalysed hydrolysis...

The reaction of nitrilimine 6a with ethyl pyridine-2-acetate (7) gave the corresponding pyrrolo[1,2-a]pyridine 8, while the reaction of 6b containing an ester moiety afforded the acyclic adduct 9. The reaction of 6a with 2-aminopyrimidine (10) gave the novel unexpected pyrimido[2,1-d]1,2,3,5-tetrazine 11. Acyclic adducts 16 and 17 were obtained fro...

New model 1,2,4-triazino[6,5-h]quinolines 8a – c are prepared by oxidative cyclization of the respective N-(quinolin-8-yl)amidrazone precursors 7a – c using copper(II) chloride. Interestingly, the cyclized products 8a – c were found to be arylated at N1 position. Analytical and spectral (MS, NMR) data of the title products are in compliance with th...

Ethyl 7,8-diamino-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (6) and its free acid 7 are prepared by chemical reduction of the respective 7-azido-8-nitroquinoline 5. Consecutive nucleophilic addition and cyclocondensation reactions of 6 with α-acetyl-N-arylhydrazonoyl chlorides 8a - c in ethanol and triethylamine are site-selec...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Model tetrahydro[1,4]thiazino[2,3-h]quinoline-8-carboxylic acids (7a-c) are synthesized via reductive lactamisation, using sodium dithionite, of the respective 7-[(carboxyalkyl)thio]-8-nitro-1,4-dihydroquinolines (5a-c). The latter compounds are made accessible via the reaction of 7-chloro-l-cyclopropyl-6-flouro-8-nitro-4-oxo-1, 4-dihydroquinoline-...

Substituted [1,4]thiazepino[2,3-h]quinolinecarboxylic acid 3 is prepared by PPA-catalyzed thermal lactamization of the respective 8-amino-7-[(2-carboxyethyl)thio]-1,4-dihydroquinoline-3-carboxylic acid 9. The latter synthon is obtained by reduction of the 8-nitro-1,4-dihydroquinoline precursor 8 which, in turn, is made accessible via interaction of...

Model tetrahydropyrido[3',2':4,5]thieno[2,3-b][1,4]thiazines 9a-c were synthesized via reductive lactamization, using sodium dithionite, of the respective 2-[(carboxyalkyl)thio]-3-nitro-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acids 7a-c. The latter derivatives were made via interaction of 2-chloro-7-cyclopropyl-3-nitro-4,7-dihydrothieno[2,3-b...

The synthesis and characterization of a series of 5-aryl-1,3,4-oxadiazol-2-yl- diphenylmethanols (4) was achieved by oxidative cyclization of N'-(3-aryl)methylene]-2-hydroxy- 2,2-diphenylacetohydrazides (3) with lead(IV) acetate. The S-{5-[hydroxy (diphenyl)methyl]-1,3,4- oxadiazol-2-yl}-aryl carbothioates (7) were prepared by the reaction of (5-me...

(5-Mercaptotetrazol-1-yl)acetic acid - nitrile imine acyclic adducts (12a-c) undergo intramolecular cyclocondensation, induced by 1,1′-carbonyldiimidazole (CDI), to afford the respective dihydrotetrazolo[5,1-c]-[1,2,4]triazines (13a-c). The formation of the latter bicycles implies that 12a-c eject H2O and undergo S→N migration (Smiles rearrangement...

Direct interaction between model anilines and an 1,3-dipolar nitrile imine, derived from 2-[N′-(1-chloro-2-oxopropylidine)hydrazine]benzoic acid, yielded the respective acyclic amidrazones. The latter adducts underwent CDI-induced cyclocondensation involving the hydrazone–NH terminus and the activated carboxy group to produce the corresponding dihy...

3-Mercaptopropionic acid-nitrile imine acyclic adducts (6a-c) undergo cyclocondensation with 1,1'-carbonyldiimidazole to afford the respective 1,3,4-thiadiazol-2-(3H)-ones (7a-c). Corresponding 1,3,4-thiadiazol-2(3H)-thiones (8a-c) were likewise produced from 6a-cand 1,1'-thiocarbonyldiimidazole, with consequent elimination of the propionate moiety...

Nitrilimines prepared from N-arylhydrazono chlorides reacted with 2-mercaptonicotinic acid yielding the corresponding addition products, 2-[(2-oxo-1-arylhydrazonopropan-1-yl)mercapto] nicotinic acids, which were treated with 1,1-carbonyldiimidazole in THF affording by cyclocondensation the corresponding hitherto unknown 2-arylhydrazono-3-oxothieno[...

γ-Aminobutyric acid (GABA) adds onto nitrile imine 1,3-dipolar species (generated in situ from their N-arylhydrazonoyl chloride precursors 1a-c) to deliver the corresponding acyclic amidrazone adducts 1Oa-c. In the presence of 1,1′-carbonyldiimidazole, the latter adducts undergo cyclocondensation involving the activated carboxyl and the amidrazone-...

For Abstract see ChemInform Abstract in Full Text.

Nitrilimines were prepared from N-arylhydrazono chlorides and reacted with ß-alanine yielding the corresponding amidrazones, which were treated with 1,1'-carbonyldiimidazole in THF affording the hitherto unknown 3-acetyl-1-aryl-1,4,5,6-tetrahydro-1,2,4-triazepin-7-ones.

For Abstract see ChemInform Abstract in Full Text.

γ -Aminobutyric acid (GABA) adds onto nitrile imine 1,3-dipolar species (generated in situ from their N-arylhydrazonoyl chloride precursors 1a-c ) to deliver the corresponding acyclic amidrazone adducts 10a-c. In the presence of 1,1’-carbonyldiimidazole, the latter adducts undergo cyclocondensation involving the activated carboxyl and the amidrazon...

The tautomerism of 4-methyldihydro-1,3,4-benzotriazepin-5-ones (2,3) is re-investigated by means of X-ray diffraction and quantum chemical calculations. The data revealed that the model compound (2a) exists in the amidrazone 1,4-dihydro tautomeric form (A), but not in the alternate 3,4-dihydro tautomer (B) as was previously reported.

In the presence of triethylamine, 2-mercaptobenzoic acid readily adds onto acylhydrazonoyl chlorides (1a–c) (precursors of the reactive nitrile imine 1,3-dipolar species) to afford good yields of the corresponding 2-[(2-oxo-1-arylhydrazonopropan-1-yl)mercapto]benzoic acids (2a–c). The latter acyclic adducts, in THF in the presence of 1,1′-carbonyld...

For Abstract see ChemInform Abstract in Full Text.

Single X-Ray crystal structure determination of dihydro-5H-1,3,4-benzotriazepin-5-one (2b) revealed that the mobile hydrogen is σ-bonded to N1, while the double bond is situated between C2-N3. In this prevailing 1,4-dihydro tautomer (2A) (preferred over the alternate 3,4-dihydro form 2B), both azomethine C2-N3 atoms are folded away, out of the plan...

2‐Aminobenzoic acid reacts readily, in the presence of triethylamine, with hydrazonoyl chlorides ( 5a‐c ) (precursors of the reactive nitrile imine 1,3‐dipolar species) to afford high yields of the corresponding acyclic amidrazone adducts ( 6a‐c ). The latter adducts undergo, in THF in presence of 1,1‐carbonyldiimida‐zole, smooth intramolecular cyc...

An approach for the synthesis of moenomycin A12C-glycoside partial structures is reported based on allyltin chemistry.

C-Phenylaminocarbonyl-N-arylnitrilimines (2) react with alkanone and cycloalkanone hydrazones (3) carrying electron-withdrawing groups (CH3CO-, PhCO- and CH3OCO-) to give the cycloaddition products 4,5-di- hydro-1,2,4-triazoles (4a-l) rather than the 1,2,4,5-tetrazines cyclo- condensation products (5a-l). The spectral data of title compounds are di...