Studies on the synthesis, in vitro antitumor activity of 4H-benzo[h]chromene, 7H-benzo[h]chromene[2,3-d]pyrimidine derivatives and structure–activity relationships of the 2-,3- and 2,3-positions

El‐Agrody, Ahmed M.; Fouda, Ahmed M.; Al-Dies, Al-Anood M.

doi:10.1007/s00044-013-0904-x

Cited by 55 publications

(23 citation statements)

References 34 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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“…Furthermore, formation of fused pyrimidinone derivatives from reaction of 2‐aminonitrile with formic acid was studied earlier . In this work, the target compound 3 was synthesized by heating of compound 1 with formic acid under reflux, and the reaction was expected to occur through intermediate amide formation arising from incomplete hydrolysis of C≡N group followed by intramolecular cyclization.…”

Section: Resultsmentioning

confidence: 99%

“…A survey in literature revealed that thermal condensation of 2‐aminonitriles with acetic anhydride yielded different products according to the reaction condition and time . Herein, compound 1 was heated under reflux with acetic anhydride for 15 h to afford both diacetylated derivative 6 together with cyclic thienopyrimidinone derivative 7 that was expected to be produced via Dimroth rearrangement.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

Hassan

Husseiny

2019

Journal of Heterocyclic Chem

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In an attempt to establish novel candidate with promising anticancer activity, two derivatives of (benzo[d]thiazol‐2‐yl)thiophene backbone 1 and 14 were synthesized, and they further reacted with various chemical reagents to afford the corresponding substituted thiophene derivatives 6, 8, 10, 15, 17, and 20, thieno[3,2‐d]pyrimidine derivatives 2–5, 7, 9, 16, 21, 23, and 24, thieno[3,2‐b]pyridine derivatives 11–13, and thieno[3,2‐e][1,4]oxazepine derivative 18. Structures of prepared compounds were affirmed via spectral and elemental data. Among the obtained compounds, seven derivatives 2, 3, 4, 5, 11, 12, and 13 were chosen by National Cancer Institute, USA. Such compounds were screened for their antitumor activity versus 60 cancer cell lines in one‐dose (10 μmol) screening assay. The outcomes showed that all selected compounds exhibited moderate to high anticancer activity towards many cancer cell lines among which compounds 5 and 11 exerted potent antitumor activity against numerous malignant growth cell lines particularly Ovarian Cancer IGROV1.

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“…Moreover, compound 2 , reacted with triethyl orthoformate to give the corresponding ethoxymethylene amino derivative 11 , which used as precursor for the preparation of the key compound 12 via cyclization with hydrazine hydrate, as depicted in Scheme . On the other hand, reaction of 2 with triethyl orthoformate in Ac 2 O gave ethyl 3‐formamido‐1,4‐dihydroquinoxaline‐2‐carboxylate ( 14 ) , instead of ethyl 3‐((ethoxymethylene)amino)‐1,4‐dihydroquinoxaline‐2‐carboxylate ( 11 ) (Scheme ). The 1 H NMR spectra of 12 revealed the presence of singlet at 4.57 ppm for NH 2 protons, in addition to the two imino protons at 12.36 and 12.71 ppm.…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Some New Quinoxaline‐Based Heterocycles

Azab

Elkanzi

Gobouri

2017

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).Considering quinoxaline as a privileged structure for developing probes of impressive therapeutic potentials, some new azole and azine conjugates of quinoxaline were synthesized. Thus, ethyl 3-amino-1,4-dihydroquinoxaline-2-carboxylate (2) was prepared as one-pot three-component product and incorporated in a series of manipulations including cyclocondensation reactions to afford a series of pharmacophoric motif conjugates 8-12, 14, 15-17, 20-23, 24-29, 30-37, and 38-43 in fair yields. The newly synthesized were characterized by IR, 1 H NMR, 13 C NMR, and mass spectral data.

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Studies on the synthesis, in vitro antitumor activity of 4H-benzo[h]chromene, 7H-benzo[h]chromene[2,3-d]pyrimidine derivatives and structure–activity relationships of the 2-,3- and 2,3-positions

Cited by 55 publications

References 34 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 and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

Design and Synthesis of Some New Quinoxaline‐Based Heterocycles

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