Synthesis, antitumor activity, and structure–activity relationship of some 4H-pyrano[3,2-h]quinoline and 7H-pyrimido[4′,5′:6,5]pyrano[3,2-h]quinoline derivatives

El‐Agrody, Ahmed M.; Abd-Rabboh, Hisham S.M.; Al-Ghamdi, Abdullah M.

doi:10.1007/s00044-012-0142-7

Cited by 47 publications

(16 citation statements)

References 41 publications

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“…Several synthetic methods have been widely applied for synthesis of pyran-based heterocyclic compounds, using many homogeneous or heterogeneous organic, inorganic, and nanomaterial catalysts, for example hexamethylenetetramine (HMT) [40], heteropolyacid [41], diammonium hydrogen phosphate [42], DBU [43], piperidine [44][45][46][47], tetrabutylammonium bromide (TBAB) [48], ionic liquids [49], morpholine [50], 4-(dimethylamino)pyridine (DMAP) [51], urea [52], 3-hydroxypropanaminium acetate (HPAA) [53], N-propylpiperazine sodium n-propionate (SBPPSP) [54], silica gel [55], sulfonic acid-functionalized silica [ [60], meglumine [61], I 2 /K 2 CO 3 [62], cetyltrimethylammonium bromide (CTABr) [63], nano-sized MgO [64], nano-structured Na 2 CaP 2 O 7 [65], NaHCO 3 [66], Na 2 CO 3 [67], triazine-functionalized ordered mesoporous organosilica [68], potassium phosphate tribasic trihydrate [69], Mg/Al hydrotalcite [70], Amberlyst A21 [71], DABCO [72], CeO 2 /CaO nanocomposite oxide [73], triton B [74], tetrabutylammonium chloride (TBAC) [75], nano-eggshell powder [76], basic alumina [77], [bmim]OH [78,79], LiBr [80], glycine [81], silica nanoparticles [82], ionic liquid choline chlorid...…”

Section: Introductionmentioning

confidence: 99%

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Kiyani

Ghorbani

2014

Res Chem Intermed

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A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the threecomponent tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50°C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in a,b-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyranannulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.

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Section: Introductionmentioning

confidence: 99%

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Kiyani

Ghorbani

2014

Res Chem Intermed

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“…Gram‐negative cell walls contain a thin peptidoglycan layer (without teichoic acids) that is surrounded by a thick plasma membrane. Hence, penetration through thin peptidoglycan layer is possible due to the presence of acid functions of these compounds .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of New Pyrano‐fused Quinolines as Antibacterial and Antimicrobial Agents

Watpade

Bholay

Toche

2017

Journal of Heterocyclic Chem

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This manuscript describes a brief overview of latest research involving the use of pyrano‐fused quinolines as new antibacterial and antimicrobial agents. The synthesis begins with 4‐hydroxy quinolone‐2‐one 1a and 6‐fluoro‐4‐hydroxyquinolin‐2(1H)‐one 1b, which were obtained by condensation of aromatic amines with diethyl malonate. 9‐Fluoro‐6H‐pyrano[3,2‐c]quinoline‐2,5‐dione 3b and 6H‐pyrano[3,2‐c]quinoline‐2,5‐dione 3a were obtained by reaction with diethyl malonate in presence of ammonium acetate. These pyranoquinolones on refluxing in phosphorous oxychloride were converted to 5‐chloro‐2H‐pyrano[3,2‐c]quinolin‐2‐one 4a and 5‐chloro‐9‐fluoro‐2H‐pyrano[3,2‐c]quinolin‐2‐one 4b in good yields. The chloro functionality in compound 4a and 4b, which are reactive, can be replaced by various nucleophilic reagents such as amines and amino acids. The resulted amino pyrano[3,2‐c]quinolines showed moderate‐to‐excellent antibacterial and antimicrobial activity.

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“…Pyranoquinoline moiety is present in many alkaloids that have attracted great attention because of their interesting biological and pharmacological properties, such as antitumor , antimicrobial , anti‐inflammatory , antiallergic , antimalarial inhibition of calcium signaling , and platelet aggregation .…”

Section: Introductionmentioning

confidence: 99%

One‐pot, Three‐component Synthesis of a New Series of 2‐Amino‐4‐aroyl‐5‐oxo‐5,6‐dihydro‐2H‐pyrano[3,2‐c]quinoline‐3‐carbonitrile in the Presence of SBA‐15 as a Nanocatalyst

Khalafy

Arlan

Chalanchi

2017

Journal of Heterocyclic Chem

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One‐pot, three‐component reaction of arylglyoxals, malononitrile and 4‐hydroxyquinolin‐2(1H)‐one in the presence of SBA‐15 as a nanocatalyst and using green solvent systems under various temperatures afforded the 2‐amino‐4‐aroyl‐5‐oxo‐5,6‐dihydro‐2H‐pyrano[3,2‐c]quinoline‐3‐carbonitrile derivatives. The best yield (70‐96%) were obtained using 20% mol of SBA‐15 as a nanocatalyst in H2O/EtOH (1:1) at 80 °C. The simplicity of work up procedure, using green solvent system, and good to excellent yields of products are the main advantages of this synthetic strategy.

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Synthesis, antitumor activity, and structure–activity relationship of some 4H-pyrano[3,2-h]quinoline and 7H-pyrimido[4′,5′:6,5]pyrano[3,2-h]quinoline derivatives

Cited by 47 publications

References 41 publications

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Synthesis of New Pyrano‐fused Quinolines as Antibacterial and Antimicrobial Agents

One‐pot, Three‐component Synthesis of a New Series of 2‐Amino‐4‐aroyl‐5‐oxo‐5,6‐dihydro‐2H‐pyrano[3,2‐c]quinoline‐3‐carbonitrile in the Presence of SBA‐15 as a Nanocatalyst

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