Synthesis of Some Thienopyrimidine Derivatives

El-Baih, Fatma E.M.; Al-Blowy, Hanan A. S.; Al-Hazimi, Hassan M.

doi:10.3390/11070498

Cited by 37 publications

(29 citation statements)

References 17 publications

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“…The reaction of cyclohexanone with ethyl cyanoacetate produced ethyl 2‐amino‐4,5,6,7‐tetrahydrobenzothiophene‐3‐carboxylate ( 9 ) which was further cyclized with formamide to afford the thieno[2,3‐ d ]pyrimidin‐4(3 H )‐one intermediate ( 10 ) . The latter was chlorinated using phosphorous oxychloride to produce 4‐chloro derivative which was used directly in the next reaction due to its high reactivity.…”

Section: Resultsmentioning

confidence: 99%

“…Similarly, Gewald procedure was applied using cyclohexanone, malononitrile, sulphur powder, and piperidine in water bath to synthesize the 4,5,6,7-tetrahydrobenzothiophene precursor (6) which was reacted in the same manner with DMF-DMA and then cyclized with intermediates 2a-h to yield the target compounds 8a-h (Scheme 3). The reaction of cyclohexanone with ethyl cyanoacetate produced ethyl 2-amino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylate (9) [20] which was further cyclized with formamide to afford the thieno [2,3-d] [23]. The latter was chlorinated using phosphorous oxychloride to produce 4-chloro derivative which was used directly in the next reaction due to its high reactivity.…”

Section: Chemistrymentioning

confidence: 99%

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Design and Synthesis of 4‐Anilinothieno[2,3‐d]pyrimidine‐Based Compounds as Dual EGFR/HER‐2 Inhibitors

Hadi

Lasheen

Hassan

et al. 2016

Archiv der Pharmazie

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Dual inhibition of the epidermal growth factor receptor (EGFR) and the human epidermal growth factor receptor 2 (HER-2) is an attractive cancer therapeutic approach. In this study, new series of 4-anilinothieno[2,3-d]pyrimidines were designed, synthesized, and tested as dual EGFR/HER-2 kinase inhibitors. Five compounds (8a, 8b, 8e-g) demonstrated low to submicromolar inhibition of both kinases with IC values of 1.2, 0.6, 0.3, 0.2, 0.4 μM and 8.2, 3.4, 1.3, 0.5, 2.7 μM for the EGFR and HER-2, respectively. Introduction of a 5,6-tetramethylene moiety into the thienopyrimidine core bearing a 4-(3-fluorobenzyloxy)-3-chloroaniline tail resulted in a favorable increase in both the EGFR and HER-2 inhibitory activities. Compound 8f (IC EGFR/HER-2: 0.2/0.5 μM) also exhibited significant cell growth inhibition on some specific NCI cell lines, especially ovarian, breast, non-small-cell lung cancer, and renal cancer cell lines.

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Section: Resultsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Design and Synthesis of 4‐Anilinothieno[2,3‐d]pyrimidine‐Based Compounds as Dual EGFR/HER‐2 Inhibitors

Hadi

Lasheen

Hassan

et al. 2016

Archiv der Pharmazie

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“…On the other hand, compounds 7 and 8 could be obtained following different reaction pathways via the procedure reported by El-Baih et al [26]. Thus, 7 could be obtained when the thiourea derivative 5 was heated under reflux in ethanolic sodium hydroxide giving the sodium salt 10 which gave 7 upon acidification with hydrochloric acid (Scheme 4).…”

Section: Resultsmentioning

confidence: 99%

Pyridine-Based Heterocycles. Synthesis of New Pyrido [4',3':4,5]thieno[2,3-d]pyrimidines and Related Heterocycles

et al. 2010

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The synthesis of the title compounds was achieved using ethyl 2-amino-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate (1) as starting material. The reaction of the amino ester 1 with phenylisothiocyanate in boiling ethanol afforded the thiourea derivative 5. The cyclization reactions of 5 under different reaction conditions led to different pyridothienopyrimidine derivatives. Other reactions of the latter derivatives leading to pyrido[4',3':4,5]thieno[2,3-d]triazolo[1,5-a]pyrimidines are also presented.

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“…Investigation of these two transformations are carried out as per the reported method using cyclohexanone and α-tetralone analogous. 10,11 The results reveals the corresponding carbonitrile functional group contains the expected Michael product.…”

Section: Figure 1 Ortep For Compound 5bmentioning

confidence: 93%

Unexpected regiospecific Michael addition product: synthesis of 5,6-dihydrobenzo[1,7]phenanthrolines

et al. 2015

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COMMUNICATION This journal isThe unexpected formation of 5,6-dihydrobenzo[1,7]phenanthroline instead of 5,6-dihydrobenzo[1,7]phenanthroline-3-carbonitrile has been observed in acridine molecules for the first time using Michael addition methodology. Moreover, we have identified Montmorillonite KSF clay as catalyst to offer regiospecific expected dihydrobenzo[1,7]phenanthroline-3-carbonitrile product and NaH base as regiospecific formation of unexpected Michael addition 5,6-dihydrobenzo[1,7]phenanthroline products. On the basis of systematic study, the novel regiospecificity could be assigned by utilization of suitable catalyst.

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Synthesis of Some Thienopyrimidine Derivatives

Cited by 37 publications

References 17 publications

Design and Synthesis of 4‐Anilinothieno[2,3‐d]pyrimidine‐Based Compounds as Dual EGFR/HER‐2 Inhibitors

Design and Synthesis of 4‐Anilinothieno[2,3‐d]pyrimidine‐Based Compounds as Dual EGFR/HER‐2 Inhibitors

Pyridine-Based Heterocycles. Synthesis of New Pyrido [4',3':4,5]thieno[2,3-d]pyrimidines and Related Heterocycles

Unexpected regiospecific Michael addition product: synthesis of 5,6-dihydrobenzo[1,7]phenanthrolines

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