- BARBITURIC ACID DERIVATIVES AS SELF-TANNING SUBSTANCES
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The present invention relates to the use of barbituric acid derivatives of the formula I as self-tanning substance, for increasing melanin synthesis, for improving melanin transport and/or improving the distribution of melanin in superbasal layers, to preparations comprising these barbituric acid derivatives, and to specific barbituric acid derivatives.
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Paragraph 0226-0227
(2020/02/20)
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- 2-Phenyl-2,3-dihydrobenzo[ d ]thiazole: A Mild, Efficient, and Highly Active in situ Generated Chemoselective Reducing Agent for the One-Pot Synthesis of 5-Monoalkylbarbiturates in Water
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A metal- and catalyst-free reductive alkylation protocol for the one-pot synthesis of 5-monoalkylbarbiturates from barbituric acids and aldehydes using the in situ generated chemoselective reducing agent 2-phenyl-2,3-dihydrobenzo[ d ]thiazole from 2-aminothiophenol and benzaldehyde is described. The notable advantages of the protocol are operational simplicity, mild reaction conditions, high yield, short reaction time, and simple workup and purification process which make it highly attractive.
- Kalita, Subarna Jyoti,Deka, Dibakar Chandra
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p. 477 - 482
(2017/12/06)
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- Ruthenium-catalyzed selective synthesis of monoalkylated barbituric acids through “borrowing hydrogen” methodology
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An environmentally benign alkylation of barbituric acids via “borrowing hydrogen” process with ruthenium catalysis has been established. The corresponding 5-(alkyl)barubituric acids were obtained in good to excellent yields with low catalyst loading. Vari
- Putra, Anggi Eka,Oe, Yohei,Ohta, Tetsuo
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supporting information
p. 1098 - 1101
(2017/03/02)
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- Design, synthesis and in vivo evaluation of sodium 2-benzyl-chloromalonates as new central nervous system depressants
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This work describes the design, synthesis and in vivo evaluation of new central nervous system depressing agents that show low levels of acute toxicity as well as high solubility in water and exhibit anxiolytic and hypnotic effects. These new compounds are sodium 2-benzyl-2-chloromalonates, which were designed using molecular modelling techniques and synthesized in four steps, with an overall yield between 41% and 65%. In vivo tests with mice, including pentobarbital-induced sleep, rotarod, open field and elevated plus maze tests, were carried out, and the results indicated that some of these agents induce activities similar to those induced by diazepam but with lower hypnotic potency and greater anxiolytic potency. These compounds were also orally administered to mice in doses of 2 g kg-1, and their effects were evaluated for 14 days. The mice did not show signs of intoxication, confirming that sodium 2-benzyl-2-chloromalonates exhibit low levels of acute toxicity. These observations indicate that sodium 2-benzyl-2-chloromalonates and their analogues are efficient and safer central nervous system depressing drugs relative to existing standards of care.
- Vieira, Andreia Aguiar,Marinho, Bruno Guimar?es,De Souza, Luana Gon?alves,Fernandes, Patricia Dias,Figueroa-Villar, José D.
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p. 1427 - 1437
(2015/08/18)
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- N-HYDROXYLAMINO-BARBITURIC ACID DERIVATIVES AS NITROXYL DONORS
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The present disclosure provides N-hydroxylamino-barbituric acid compounds of formulae (1)- (4), pharmaceutical compositions and kits comprising them, and methods of using such compounds or pharmaceutical compositions. The present disclosure provides methods of using such compounds or pharmaceutical compositions for treating heart failure.
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Page/Page column 142-145
(2015/12/17)
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- Pd/C-catalyzed alkylation of heterocyclic nucleophiles with alcohols through the "borrowing hydrogen" process
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The alkylation of heterocyclic compounds is important for the synthesis of various biologically active compounds. In this paper, we present the development of a Pd/C-catalyzed alkylation of heterocyclic compounds using alcohols as the alkylating agents. T
- Putra, Anggi Eka,Oe, Yohei,Ohta, Tetsuo
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p. 7799 - 7805
(2015/12/31)
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- Nuclear magnetic resonance and molecular modeling study of exocyclic carbon-carbon double bond polarization in benzylidene barbiturates
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Benzylidene barbiturates are important materials for the synthesis of heterocyclic compounds with potential for the development of new drugs. The reactivity of benzylidene barbiturates is mainly controlled by their exocyclic carbon-carbon double bond. In this work, the exocyclic double bond polarization was estimated experimentally by NMR and correlated with the Hammett σ values of the aromatic ring substituents and the molecular modeling calculated atomic charge difference. It is demonstrated that carbon chemical shift differences and NBO charge differences can be used to predict their reactivity.
- Figueroa-Villar, J. Daniel,Vieira, Andreia A.
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p. 310 - 317
(2013/03/13)
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- Synthesis and in vivo evaluation of 5-chloro-5-benzobarbiturates as new central nervous system depressants
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A new family of barbiturates, 5-chloro-5-benzylbarbituric acids, was prepared using a simple efficient synthetic method from aromatic aldehydes and barbituric acid, followed by reduction and chlorination with trichloro-isocyanuric acid, affording overall yields of 53 to 70percent. The in vivo evaluation with mice showed that these compounds present tranquilizing activity.
- Vieira, Andreia A.,Gomes, Niele M.,Matheus, Maria E.,Fernandes, Patricia D.,Figueroa-Villar, Jose? D.
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p. 364 - 371
(2011/10/01)
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- Exploring new inhibitors of Plasmodium falciparum purine nucleoside phosphorylase
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Plasmodium falciparum purine nucleoside phosphorylase (PfPNP) has a central role in purine salvage and inhibitors of the enzyme have been shown to have antiplasmodial activity. The enzyme preferentially uses inosine as substrate (Km = 5 μM, ks
- Cui, Huaqing,Ruda, Gian Filippo,Carrero-Lérida, Juana,Ruiz-Pérez, Luis M.,Gilbert, Ian H.,González-Pacanowska, Dolores
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experimental part
p. 5140 - 5149
(2010/11/19)
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- Multi-catalysis cascade reactions based on the methoxycarbonylketene platform: Diversity-oriented synthesis of functionalized non-symmetrical malonates for agrochemicals and pharmaceuticals
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In this paper we describe new multi-catalysis cascade (MCC) reactions for the one-pot synthesis of highly functionalized non-symmetrical malonates. These metal-free reactions are either five-step (olefination/hydrogenation/alkylation/ ketenization/esterif
- Ramachary, Dhevalapally B.,Venkaiah, Chintalapudi,Reddy, Y. Vijayendar,Kishor, Mamillapalli
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scheme or table
p. 2053 - 2062
(2009/09/05)
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- Discovery and optimization of novel, non-steroidal glucocorticoid receptor modulators
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A virtual screening approach comprising a 3-D similarity search based on known GR modulators was used to identify a novel series of non-steroidal glucocorticoid receptor (GR) antagonists. Optimization of the initial hit to provide potent compounds which e
- Ray, Nicholas C.,Clark, Robin D.,Clark, David E.,Williams, Karen,Hickin,Crackett, Peter H.,Dyke, Hazel J.,Lockey, Peter M.,Wong, Melanie,Devos, Rene,White, Anne,Belanoff, Joseph K.
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p. 4901 - 4905
(2008/12/22)
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- Modified pyrimidine glucocorticoid receptor modulators
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The present invention provides a novel class of modified pyrimidine compounds and compositions and methods of using the compounds as glucocorticoid receptor modulators.
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Page/Page column 17
(2008/06/13)
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- A novel and green protocol for two-carbon homologation: A direct amino acid/K2CO3-catalyzed four-component reaction of aldehydes, active methylenes, Hantzsch esters and alkyl halides
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A novel and green approach for the two-carbon homologation of aldehydes using amino acid catalysis has been developed and further extended to the generation of pharmaceutically active cyano-esters via four-component reactions in one-pot.
- Ramachary, Dhevalapally B.,Kishor,Ramakumar
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p. 651 - 656
(2007/10/03)
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- Mono C-alkylation and mono C-benzylation of barbituric acids through zinc/acid reduction of acyl, benzylidene, and alkylidene barbiturate intermediates
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Through systematic exploration of reaction conditions, very efficient preparative procedures for obtaining large quantities of substituted 5-alkyl and 5-benzylbarbituric acids were developed. The procedure involves a two step preparation in which the second step is zinc dust/acid reduction. For preparation of 5-alkylbarbiturates, the first step is the preparation of either 5-acyl or 5-alkylidenebarbiturate. If 5-benzylbarbiturate is the target product, then the first step includes the preparation of 5-benzylidene. Regardless of the nature of the first step, all reactions presented synthetic yields around 90% and isolation and purification involves only crystallization.
- Jursic, Branko S.,Stevens, Edwin D.
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p. 2203 - 2210
(2007/10/03)
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- Barbituric acid derivatives with antimetastatic and antitumor activity
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The invention is directed to barbituric acid derivatives having inhibitory activity for matrix maetalloproteases comprised of formula (I): pharmaceutical compositions thereof, processes for preparing the derivatives, and methods for treating diseases associated with elevated or uncontrolled levels of matrix metalloprotease activity, e.g., cancer, specifically tumor progression and tumor metastasis, inflammation, or as a method of contraception.
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Page column 11
(2010/01/21)
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- Reductive C-alkylation of barbituric acid derivatives with carbonyl compounds in the presence of platinum and palladium catalysts
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Effective synthetic procedures for the preparation of mono- and di-C-alkylated barbituric acid derivatives through palladium and platinum catalytic hydrogenation of solutions of barbituric acids (unsubstituted, N-mono, and N,N′-disubstituted barbituric acids) and carbonyl compounds (aliphatic and aromatic aldehydes and ketones).
- Jursic, Branko S.,Neumann, Donna M.
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p. 4103 - 4107
(2007/10/03)
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- Barbituric acid derivatives, processes for their production and pharmaceutical agents containing these compounds
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PCT No. PCT/EP96/05766 Sec. 371 Date Aug. 26, 1998 Sec. 102(e) Date Aug. 26, 1998 PCT Filed Dec. 20, 1996 PCT Pub. No. WO97/23465 PCT Pub. Date Jul. 3, 1997Compounds of formula I, useful as matrix metalloprotease inhibitors, wherein X, Y and Z are each oxygen; R1 is selected from the group consisting of (a) n-octyl, (b) n-decyl, (c) biphenyl and (d) (4-phenoxy)phenyl, wherein the terminal monocycle for moieties (c)-(d) is unsubstituted or substituted by a substituent selected from the group consisting of -NH2, -NO2, -SO2NH2, -SO2CH3, acetyl, hydroxy, methoxy, ethoxy, cyano and halogen; R2 and R3 are each hydrogen; and R4 and R5, together with the nitrogen atom to which they are bound, form a piperazinyl or piperidyl ring, wherein the piperazinyl ring is substituted in the 4-position with a substituent selected from the group consisting of (a) a 6-membered aromatic monocycle having 0, 1 or 2 nitrogen atoms and the remainder of the atoms in the monocycle being carbon and (b) hydroxy-C1-C6 alkyl, wherein the monocycle is unsubstituted or substituted by a substituent selected from the group consisting of halogen, -NH2, -NO2, -SO2NH2, -SO2CH3, acetyl and cyano.
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- Derivatives of 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-phenyluracil and 5-benzyluracil synthesis and biological properties
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A number of 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil and -cytosine nucleosides substituted at the 5 position with a nitrophenyl or nitrobenzyl group were synthesized from 5-phenyl- and 5-benzyluracil via condensation of the fluorinated sugar, followed by nitration. The corresponding amino analogues were also prepared by reduction of the nitro nucleosides. The uracil nucleosides were converted into the corresponding cytosine nucleosides by way of the triazole intermediates. None of these nucleosides exhibited significant activity against herpes simplex virus type 1 in Vero cells. However, cytosine nucleosides containing the o-nitrophenyl, p-nitrophenyl, p- nitrobenzyl or p-aminobenzyl substituent were found to be toxic (even at 1 μM) to uninfected Vero cells, although they were essentially nontoxic in HL- 60 cells. The 5'-monophosphates of the uracil nucleosides were inhibitors of the reaction catalyzed by purified Ehrlich ascites carcinoma thymidylate synthase, the 5-phenyluracil nucleotides causing a strong inhibition, competitive vs dUMP, described by the K(i) value of 0.01 μM.
- Dziewiszek,Schinazi,Chou,Su,Dzik,Rode,Watanabe
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- Synthesis of a New Class of Uridine Phoshorylase Inhibitors
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A new series of potent uridine phosphorylase inhibitors have been prepared from barbituric acid.Among them 1--5-(m-benzyloxy)benzylbarbituric acid (37, BBBA) is the most promising having a Ki value of 1.1 +/- 0.2 nM wit
- Tzeng, Cherng-Chyi,Panzica, Raymond P.,Naguib, Fardos N.M.,Kouni, Mahmoud H. el
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p. 1399 - 1404
(2007/10/02)
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