Syntheses and antiinflammatory activity of malonamic acid, malonamate and malonamide derivatives of some heterocyclic compounds.

Katagi, Toyoshi; Aoki, M.; Kashiwagi, Masako; Ohata, Katsuya; Kohno, Shigekatsu; Murata, Tamotsu; Inoi, Takeshi

doi:10.1248/cpb.33.4878

Cited by 17 publications

(11 citation statements)

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“…156 The anhydride of monoethyl malonate, prepared using DCC, has been employed (without isolation) for couplings outside the PMRI peptide field, but the yields were only moderate. 157,158 Some of the theoretical advantages of mixedanhydride couplings (i.e., easily removable byproducts) may be obtained by using reagents that are carbonic acid derivatives wherein both leaving groups are auxiliary nucleophiles: any side reaction analogous to that depicted in Scheme 25 is then immaterial for it merely generates an activated coupling species. Such reagents are yet to find widespread use in PMRI peptide synthesis (but see section VI.A.2.c).…”

Section: Scheme 5 Formation Of Byproducts During the Synthesis Of Bimentioning

confidence: 99%

“…Such reagents are yet to find widespread use in PMRI peptide synthesis (but see section VI.A.2.c). Nevertheless, carbonyldiimidazole has been used to couple monoesters of malonic acid with amines (albeit in poor yields), 157 and we have used the reagent N,N′-disuccinimidyl carbonate, developed by Ogura et al, to prepare the HOSu active ester of a PMRI dipeptide in good yield. 109,159 In contrast to malonic anhydrides, monochlorides of malonic acids are readily accessible by conventional methods and couple to R-amino acids and peptides with varying efficiency (e.g., see refs 152, 160, and 161).…”

Section: Scheme 5 Formation Of Byproducts During the Synthesis Of Bimentioning

confidence: 99%

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Partially Modified Retro-Inverso Peptides: Development, Synthesis, and Conformational Behavior

1998

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Section: Scheme 5 Formation Of Byproducts During the Synthesis Of Bimentioning

confidence: 99%

Section: Scheme 5 Formation Of Byproducts During the Synthesis Of Bimentioning

confidence: 99%

Partially Modified Retro-Inverso Peptides: Development, Synthesis, and Conformational Behavior

1998

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“…166 -168 ºC). 20 It should be mentioned that the other reported synthesis of 2 afforded a 5% yield by a different procedure. 20 Flash vacuum pyrolysis of 1.…”

Section: Synthesis Of Ethyl 3-oxo-3-(4h-124-triazol-3-ylamino)propamentioning

confidence: 97%

Flash vacuum pyrolysis of azolyl-malonamates. Synthesis of 5-hydroxy-azolopyrimidin-7-ones

Pelßez¹,

Gafarova²,

Yranzo³

2003

Arkivoc

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The synthesis and flash vacuum pyrolysis (fvp) reactions of ethyl 3-oxo-3-(1,3-thiazol-2ylamino)propanoate (1) and of ethyl 3-oxo-3-(4H-1,2,4-triazol-3-ylamino)propanoate (2) are described in this article. The synthesis of both compounds was performed by reaction of the corresponding aminoheterocycle and diethylmalonate with higher yields than previously described methodologies. Flash vacuum pyrolysis reactions of 1 were performed between 300 and 500ºC. Reactions between 300 and 430ºC afforded ethanol and 5-hydroxy-7H-[1,3]thiazolo[3,2-a]pyrimidin-7-one (3) and between 450 and 500ºC carbon suboxide (4), 2-aminothiazole (5) along with 3 and ethanol were formed. Compounds 4 and 5 were formed a higher temperatures from 3, as was demonstrated by an independent reaction of 3. Reactions of 1 over solid catalysts (zeolites and hydrotalcites) were also carried out. In both cases they afforded about 40% of 3 at 250ºC. Flash vacuum pyrolysis reactions of 2 were carried out between 300 and 450ºC. Up to 430ºC the isolated products were ethyl-3-(3-amino-1H-1,2,4-triazol-1-yl)-3-oxopropanoate (6), 5hydroxy[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one (7) and ethanol. From 430 to 450ºC decomposition of 2 by a different mechanism than reactions at lower temperatures afforded 1,2,4-triazole (8), ethoxyoxazirene (9) and probably ketene (10) (not detected). Reaction paths explaining reactions of 1 and 2 are discussed.

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“…Some of them have been used in medicine as CNS antidepressents and anti-convulsants, 16 antiantiinflammatories, 17 κ opioid receptor agonists, 18 orexin, 19 α v β 3 20 and cholecystokinin A receptor antagonists 21 as well as activators of caspases and inducers of apoptosis. 22 Also, some malonamide derivatives have been used in the treatment of Alzheimer's disease.…”

Section: A N U S C R I P Tmentioning

confidence: 99%

One-pot synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives using multi-component reactions

2014

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Syntheses and antiinflammatory activity of malonamic acid, malonamate and malonamide derivatives of some heterocyclic compounds.

Cited by 17 publications

References 0 publications

Partially Modified Retro-Inverso Peptides: Development, Synthesis, and Conformational Behavior

Partially Modified Retro-Inverso Peptides: Development, Synthesis, and Conformational Behavior

Flash vacuum pyrolysis of azolyl-malonamates. Synthesis of 5-hydroxy-azolopyrimidin-7-ones

One-pot synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives using multi-component reactions

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