Synthesis and transformations of furan derivatives

Saldabol, N. O.; Treilone, A. É.; Alekseeva, L. N.; Brizga, B. A.; Medne, K. K.

doi:10.1007/bf00768084

Pharm Chem J

1967

DOI: 10.1007/bf00768084

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Synthesis and transformations of furan derivatives

N. O. Saldabol

A. É. Treilone

L. N. Alekseeva

et al.

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Cited by 2 publications

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“…Treatment of I with phencyl bromide following the method of Saldabols et al' 14) , yielded the 2-imino-3-benzoylmethylnaphtho[2,3-d]thiazole-4,9dione hydrobromide II as a cyclic intermediate product, which on heating in absolute ethanol underwent cyclization giving 2-phenylimidazo[2 ,1 -b]naphtho[2,3-d]thiazole-5,10-dione III [Scheme 1]. The reaction of I with ethyl acrylate, ethyl acetoacetate and diethyl malonate gave the corresponding naphthothiazolopyrimidine derivatives VIII-XI.…”

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confidence: 99%

“…Treatment of I with phencyl bromide following the method of Saldabols et al' 14) , yielded the 2-imino-3-benzoylmethylnaphtho[2,3-d]thiazole-4,9dione hydrobromide II as a cyclic intermediate product, which on heating in absolute ethanol underwent cyclization giving 2-phenylimidazo[2 ,1 -b]naphtho[2,3-d]thiazole-5,10-dione III [Scheme 1]. Treatment of I with phencyl bromide following the method of Saldabols et al' 14) , yielded the 2-imino-3-benzoylmethylnaphtho[2,3-d]thiazole-4,9dione hydrobromide II as a cyclic intermediate product, which on heating in absolute ethanol underwent cyclization giving 2-phenylimidazo[2 ,1 -b]naphtho[2,3-d]thiazole-5,10-dione III [Scheme 1].…”

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confidence: 99%

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Synthesis of Heterocyclic Quinones Containing Bridgehead Nitrogen Atom from 2-Aminonaphtho[2,3-d]thiazole-4,9-dione.

Fandy¹

2000

Heterocyclic Communications

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Imidazonaphthothiazole derivatives III-VI were prepared by treatment of I with phencyl bromide, chloroacetic acid, diethyl oxalate and 2,3-dichloroquinoxaline respectively. The reaction of I with ethyl acrylate, ethyl acetoacetate and diethyl malonate gave the corresponding naphthothiazolopyrimidine derivatives VIII-XI.Imidazo[2,l-b]thiazole and its derivatives are useful heterocycles for pharmacological* " 5) . Therefore a number of methods has been developed for the preparation of these derivatives' 1 ' 3,6 '^. Quinones are also reported to have a wide variety of biological activities' 8 ' 10) . In extension of our work on the synthesis of nitrogen heterocyclic quinones' 11,12) , we report here the synthesis of fused imidazothiazolo and thiazolopyrimidinoquinone ring system and evaluation of their biological activities have been undertaken.Thus, 2,3-dichloro-l,4-naphthoquinones reacted with thiourea to give 2-aminonaphtho[2,3-d]thiazole-4,5-dione li 3) . Treatment of I with phencyl bromide following the method of Saldabols et al' 14) , yielded the 2-imino-3-benzoylmethylnaphtho[2,3-d]thiazole-4,9dione hydrobromide II as a cyclic intermediate product, which on heating in absolute ethanol underwent cyclization giving 2-phenylimidazo[2 ,1 -b]naphtho[2,3-d]thiazole-5,10-dione III [Scheme 1]. Compound III was also obtained directly by refluxing I with phencyl bromide in absolute ethanol. The reaction of I with chloroacetic acid afforded 2-hydroxyimidazo[2 ,1 -b]naphtho[2,3-d]thiazole-5,10-dione IV. On the other hand, refluxing of I with diethyl oxalate [Scheme 1] in absolute ethanol gave 2,3-dihydroimidazo[2 ,1-b]naphtho[2,3-d]thiazole-2,3,5,10-tetrone V in good yield. Compound I when refluxed with 2,3-dichloroquinoxaline in absolute ethanol gave quinoxalino[2,3:4,5 ]imidazo[2 ,1 -b]naphtho[2,3-d]thiazole-8,13-dione VI [Scheme 1], The structures of Π-VI were confirmed based on its correct microanalytical results and spectral data [cf. Table 2], 585 Brought to you by |

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mentioning

confidence: 99%

“…Treatment of I with phencyl bromide following the method of Saldabols et al' 14) , yielded the 2-imino-3-benzoylmethylnaphtho[2,3-d]thiazole-4,9dione hydrobromide II as a cyclic intermediate product, which on heating in absolute ethanol underwent cyclization giving 2-phenylimidazo[2 ,1 -b]naphtho[2,3-d]thiazole-5,10-dione III [Scheme 1]. Treatment of I with phencyl bromide following the method of Saldabols et al' 14) , yielded the 2-imino-3-benzoylmethylnaphtho[2,3-d]thiazole-4,9dione hydrobromide II as a cyclic intermediate product, which on heating in absolute ethanol underwent cyclization giving 2-phenylimidazo[2 ,1 -b]naphtho[2,3-d]thiazole-5,10-dione III [Scheme 1].…”

mentioning

confidence: 99%

Synthesis of Heterocyclic Quinones Containing Bridgehead Nitrogen Atom from 2-Aminonaphtho[2,3-d]thiazole-4,9-dione.

Fandy¹

2000

Heterocyclic Communications

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Antiproliferative Properties of Vinyl Dipeptides: Synthesis and MCF-7 Cell Line Testing

Bayoumi¹

2012

OJMC

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Peptide mimics derived with close structure to peptide have vast utility because they are expected to interfere with biological targets while having superior drug-like properties if compared to peptides. In this work, novel vinyl dipeptides which are different in a double bond between the α-carbon of peptide and C1 of its side chain. Added to that, suitable substituents were selected to harness drug-like properties. The compounds were found to have moderate activities when tested against MCF-7 breast cancer cell line. For instance, the adamantyl analogue 2-(benzoylamino)-3-(2-furyl)-N-(1-adamantyl) propenamide (1c) and the heterocyclic analogue 2-(Benzoylamino)-3-(2-furyl)-N-[2-(5-cyanothia-zol-2yl)] propenamide (1o) exhibited inhibition potency at 27.4 and 37.8 µM, respectively.

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Synthesis and transformations of furan derivatives

Cited by 2 publications

References 2 publications

Synthesis of Heterocyclic Quinones Containing Bridgehead Nitrogen Atom from 2-Aminonaphtho[2,3-d]thiazole-4,9-dione.

Synthesis of Heterocyclic Quinones Containing Bridgehead Nitrogen Atom from 2-Aminonaphtho[2,3-d]thiazole-4,9-dione.

Antiproliferative Properties of Vinyl Dipeptides: Synthesis and MCF-7 Cell Line Testing

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