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Synthesis of Five-Membered Cyclic Guanidines via Cascade [3 + 2] Cycloaddition of α-Haloamides with Organo-cyanamides
The convenient preparation of N2-unprotected five-membered cyclic guanidines was achieved through a cascade [3 + 2] cycloaddition between organo-cyanamides and α-haloamides under mild conditions in good to excellent yields (up to 99%). The corresponding cyclic guanidines could be easily transformed into hydantoins via hydrolysis.
Wang, Chuan-Chuan,Qu, Ya-Li,Liu, Xue-Hua,Ma, Zhi-Wei,Yang, Bo,Liu, Zhi-Jing,Chen, Xiao-Pei,Chen, Ya-Jing
p. 3546 - 3554
(2021/02/16)

Catalytic hydration of cyanamides with phosphinous acid-based ruthenium(ii) and osmium(ii) complexes: scope and mechanistic insights
The synthesis of a large variety of ureas R1R2NC(O)NH2 (R1 and R2 = alkyl, aryl or H; 26 examples) was successfully accomplished by hydration of the corresponding cyanamides R1R2NCN using the phosphinous acid-based complexes [MCl2(η6-p-cymene)(PMe2OH)] (M = Ru (1), Os (2)) as catalysts. The reactions proceeded cleanly under mild conditions (40-70 °C), in the absence of any additive, employing low metal loadings (1 molpercent) and water as the sole solvent. In almost all the cases, the osmium complex 2 featured a superior reactivity in comparison to that of its ruthenium counterpart 1. In addition, for both catalysts, the reaction rates observed for the hydration of the cyanamide substrates were remarkably faster than those involving classical aliphatic and aromatic nitriles. Computational studies allowed us to rationalize all these trends. Thus, the calculations indicated that the presence of a nitrogen atom directly linked to the CN bond depopulates electronically the nitrile carbon by inductive effect when coordinated to the metal center, thus favouring the intramolecular nucleophilic attack of the OH group of the phosphinous acid ligand to this carbon. On the other hand, the higher reactivity of Os vs. Ru seems to be related with the lower ring strain on the incipient metallacycle that starts to form in the transition state associated with this key step in the catalytic cycle. Indirect experimental evidence of the generation of the metallacyclic intermediates was obtained by studying the reactivity of [RuCl2(η6-p-cymene)(PMe2OH)] (1) towards dimethylcyanamide in methanol and ethanol. The reactions afforded compounds [RuCl(η6-p-cymene)(PMe2OR)(NCNMe2)][SbF6] (R = Me (5a), Et (5b)), resulting from the alcoholysis of the metallacycle, which could be characterized by single-crystal X-ray diffraction. This journal is
álvarez, Daniel,Cadierno, Victorio,Crochet, Pascale,González-Fernández, Rebeca,López, Ramón,Menéndez, M. Isabel
p. 4084 - 4098
(2020/07/09)

An efficient one-pot synthesis of industrially valuable primary organic carbamates and: N -substituted ureas by a reusable Merrifield anchored iron(ii)-anthra catalyst [FeII(Anthra-Merf)] using urea as a sustainable carbonylation source
An efficient synthesis of primary carbamates and N-substituted ureas is explored with a newly developed heterogeneous polymer supported iron catalyst in the presence of a sustainable carbonylation source. The Merrifield anchored iron(ii)-anthra catalyst [FeII(Anthra-Merf)] was synthesized by functionalization of Merrifield polymer followed by grafting of iron metal. The catalyst [FeII(Anthra-Merf)] was characterized by several techniques, like SEM, EDAX, TGA, PXRD, XPS, FTIR, CHN, AAS and UV-Vis analysis. The designed polymer embedded [FeII(Anthra-Merf)] complex is a remarkably successful catalyst for the synthesis of primary organic carbamates and N-substituted ureas by using safe carbonylation agent urea with different derivatives of alcohols and amines, respectively. The reported catalyst is a potential candidate towards contributing a satisfactory yield of isolated products under suitable reaction conditions. The catalyst is recyclable and almost non-leaching in nature after six runs with an insignificant drop in catalytic activity. Thus we found an economical and viable catalyst [FeII(Anthra-Merf)] for primary carbamates and N-substituted urea synthesis under moderate reaction conditions.
Basu, Priyanka,Dey, Tusar Kanto,Ghosh, Aniruddha,Biswas, Surajit,Khan, Aslam,Islam, Sk. Manirul
p. 2630 - 2643
(2020/02/20)

A Straightforward Synthesis of N-Substituted Ureas from Primary Amides
A direct and convenient method for the preparation of N-substituted ureas is achieved by treating primary amides with phenyliodine diacetate (PIDA) in the presence of an ammonia source (NH 3 or ammonium carbamate) in MeOH. The use of 2,2,2-trifluoroethanol (TFE) as the solvent increases the electrophilicity of the hypervalent iodine species and allows the synthesis of electron-poor carboxamides. This transformation involves a nucleophilic addition of ammonia on the isocyanate intermediate generated in situ by a Hofmann rearrangement of the starting amide.
Franck, Xavier,Glachet, Thomas,Ibert, Quentin,Lohier, Jean-Fran?ois,Reboul, Vincent,Saraiva Rosa, Nathalie
p. 2099 - 2105
(2020/07/13)

Dual palladium-photoredox catalyzed chemoselective C-H arylation of phenylureas
A highly chemoselective C-H arylation of phenylureas has been accomplished using dual palladium-photoredox catalysis at room temperature without any additives, base or external oxidants. Regioselective C-H arylation ofN,N'-diaryl substituted unsymmetrical phenylureas has also been accomplished by a careful choice of aryl groups.
Babu, Sakamuri Sarath,Shahid,Gopinath, Purushothaman
supporting information
p. 5985 - 5988
(2020/06/04)

Direct conversion of carboxylic acids to various nitrogen-containing compounds in the one-pot exploiting curtius rearrangement
Herein we report, a single-pot multistep conversion of inactivated carboxylic acids to various N-containing compounds using a common synthetic methodology. The developed methodology rendered the use of carboxylic acids as a direct surrogate of primary amines, for the synthesis of primary ureas, secondary/tertiary ureas, O/S-carbamates, benzoyl ureas, amides, and N-formyls, exploiting the Curtius reaction. This approach has a potential to provide a diversified library of N-containing compounds, starting from a single carboxylic acid, based on the selection of the nucleophile.
Kumar, Arun,Kumar, Naveen,Sharma, Ritika,Bhargava, Gaurav,Mahajan, Dinesh
p. 11323 - 11334
(2019/09/10)

A green and facile approach for the synthesis of N-monosubstituted ureas in water: Pd catalyzed reaction of arylcyanamides (an unexpected behavior of electron withdrawing groups)
The Fe3O4 magnetic nano-particles were prepared, coated with tetraethyl orthosilicate (TEOS), functionalized with 3-chloropropyltrimethoxysilane (CPTMS), further functionalized with 2,2′-(piperazine-1,4-diylbis(methylene) dianiline (PDMD) and the corresponding Pd complex synthesized as a novel nano-magnetic heterogeneous catalyst (Fe3O4@SiO2@CPTMS@PDMD@Pd) to be used for the synthesis of various N-monosubstituted ureas in water. Also, in another attempt to see the effect of HCOOH, the hydration reaction of arylcyanamide was carried out in the presence of HCOOH (water + 98% HCOOH) which had two effects: it decreased the amount of the Pd catalyst from 40 to 30 mg, and the reaction condition was changed from the reflux condition to room temperature. Interestingly, the arylcyanamides with electron withdrawing groups influence the course of the reaction and need more reaction times for completion which is an unexpected behavior, probably due to the high electron density around the central carbon atom of the nitrile group.
Habibi, Davood,Heydari, Somayyeh,Faraji, Alireza,Keypour, Hasan,Mahmoudabadi, Masoumeh
p. 520 - 529
(2018/06/26)

Superparamagnetic Fe3O4 Nanoparticles in a Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Primary Carbamates and Monosubstituted Ureas
Superparamagnetic Fe3O4 nanoparticles were used to synthesize various primary carbamates as well as monosubstituted and N,N-disubstituted ureas. This efficient phosgene-free process used urea as an eco-friendly carbonyl source in the presence of a biocompatible deep eutectic solvent (DES) to provide an inexpensive and attractive route that afforded the products in moderate to excellent yields. The employed DES serves both a catalytic role and as the green reaction medium. The magnetic nanocatalyst and DES can been reused several times without a significant loss of activity.
Inaloo, Iman Dindarloo,Majnooni, Sahar,Esmaeilpour, Mohsen
p. 3481 - 3488
(2018/07/29)

A practically simple, catalyst free and scalable synthesis of: N -substituted ureas in water
A practically simple, mild and efficient method is developed for the synthesis of N-substituted ureas by nucleophilic addition of amines to potassium isocyanate in water without organic co-solvent. Using this methodology, a variety of N-substituted ureas (mono-, di- and cyclic-) were synthesized in good to excellent yields with high chemical purity by applying simple filtration or routine extraction procedures avoiding silica gel purification. The developed methodology was also found to be suitable for gram scale synthesis of molecules having commercial application in large volumes. The identified reaction conditions were found to promote a unique substrate selectivity from a mixture of two amines.
Tiwari, Lata,Kumar, Varun,Kumar, Bhuvesh,Mahajan, Dinesh
p. 21585 - 21595
(2018/06/26)

Design and synthesis of novel N-(4-(Pyridin-2-yloxy)benzylidene)-4-[4-(substituted)phenyl]semicarbazides as potential anticonvulsant agents
A new series of N-(4-(pyridin-2-yloxy)benzylidene)-4-[4-(substituted)phenyl]semicarbazides (PSSD1-8) were designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for their possible anticonvulsant activity. All the derivatives were synthesized by the given scheme and reaction process was monitored by thin layer chromatography. The structure of synthesized derivatives was confirmed by FT-IR, 1H NMR, mass spectroscopy and elemental analysis. The anticonvulsant activity was established after intraperitoneal administration in MES and scMET seizure models. The most active compound of the series was 1-(4-(pyridin-2-yloxy)-benzylidene)-4-p-tolylsemicarbazide (PSSD5). A molecular docking study was carried out in order to assess the interaction and binding modes with target receptor/enzyme. Titled compounds were found to strongly bind to human gamma-aminobutyric acid receptor (GABAAR-β3). A computational study was also carried to predict the pharmacokinetic properties of the synthesized compounds.
Singh, Prem,Tripathi, Laxmi
p. 2193 - 2200
(2018/09/10)

Optimization of 5-arylidene barbiturates as potent, selective, reversible LSD1 inhibitors for the treatment of acute promyelocytic leukemia
Histone lysine specific demethylase 1 (LSD1) is overexpressed in diverse hematologic disorders and recognized as a promising target for blood medicines. In this study, molecular docking-based virtual screening united with bioevaluation was utilized to identify novel skeleton of 5-arylidene barbiturate as small-molecule inhibitors of LSD1. Among the synthesized derivatives, 12a exhibited reversible and potent inhibition (IC50 = 0.41 μM) and high selectivity over the MAO-A and MAO-B. Notably, 12a strongly induced differentiation effect on acute promyelocytic leukemia NB4 cell line and distinctly escalated the methylation level on histone 3 lysine 4 (H3K4). Our findings indicate that 5-arylidene barbiturate may represent a new skeleton of LSD1 inhibitors and 12a deserve as a promising agent for the further research.
Xu, Siyuan,Zhou, Chen,Liu, Rongfeng,Zhu, Qihua,Xu, Yungen,Lan, Fei,Zha, Xiaoming
p. 4871 - 4880
(2018/09/22)

Design, synthesis, and biological evaluation of hydantoin bridged analogues of combretastatin A-4 as potential anticancer agents
A series of novel hydantoin-bridged analogues of combretastatin A-4 (CA-4) were designed, synthesized and evaluated for antiproliferative activities in vitro and in vivo. The most potent compound 8d, showed potent cytotoxicity against four human cancer cell lines with IC50 values of 0.186–0.279 μM, and possessed the efficacy of inhibiting tubulin polymerization, disrupting in vitro vascularization, blocking cell cycle in G2/M phase and inducing cell apoptosis. In the nude mice xenograft model, 8d significantly inhibited the tumor growth and showed low toxicity. Further chiral separation proved (R)-(?)-8d to be the preferential enantiomer with IC50 values of 0.081–0.157 M. These results indicated that the hydantoin derivatives merit further investigation as potential anticancer agents that inhibit tubulin polymerization.
Zhang, Mao,Liang, Yu-Ru,Li, Huan,Liu, Ming-Ming,Wang, Yang
p. 6623 - 6634
(2017/11/13)

Composition for trichogenousness
The present invention relates to novel barbiturate and thiobarbiturate derivatives and a composition for promoting hair growth using the same. According to the present invention, the barbiturate and thiobarbiturate derivatives, in an animal model, have shown to promote hair growth and have excellent effects on hair growth by promoting regulation of Wnt/andbeta;-catenin and hair growth factor signaling and suppressing mechanism of apoptosis. Accordingly, the barbiturate and thiobarbiturate derivatives of the present invention may be used as a composition for promoting hair growth.COPYRIGHT KIPO 2017
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Paragraph 0382-0386

(2017/08/08)

(4-Methoxyphenyl)amine and its derivatives in the synthesis of O-silylurethanes, ureas, and formamides
Reactions of (4-methoxyphenyl)amine and its trimethylsilyl derivative with organosilicon isocyanates and phenylisocyanate have been studied. (4-Methoxyphenyl)formamide was first synthesized by the reaction of (4-methoxyphenyl)amine with ethyl formate. The structure of trimethylsilyl(4-methoxyphenyl)-carbamate and N-(4-methoxyphenyl)formamide was determined by X-ray diffraction (XRD) analysis.
Belova,Pletneva,Golub,Korlyukov,Kirilin,Petrogradskii
p. 1531 - 1535
(2017/09/01)

Transition Metal-Free Carbazole Synthesis from Arylureas and Cyclohexanones
An efficient strategy for carbazole synthesis from arylureas and cyclohexanones under transition metal-free conditions has been developed. The combined use of potassium iodide and iodine could significantly improve the reaction efficiency to provide 2,6-disubstituted 9-arylcarbazoles in moderate to good yields. In this kind of transformation, the whole carbazole moiety (except the nitrogen atom) comes from two equivalents of cyclohexanones. (Figure presented.).
Wu, Jun,Xie, Yanjun,Chen, Xiangui,Deng, Guo-Jun
supporting information
p. 3206 - 3211
(2016/10/21)

Selective and facile oxidative desulfurization of thioureas and thiobarbituric acids with singlet molecular oxygen generated from trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane
An efficient and facile procedure using trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane has been developed for oxidative desulfurization of thioureas and thiobarbituric acids. The reactions proceeded smoothly very fast under mild conditions in basic media at room temperature to afford the respective ureas in excellent yields. Simple procedure and work up, mild conditions, high yields, short reaction times, use of highly potent and non-toxic oxidant are the main merits of the present method.
Azarifar, Davood,Golbaghi, Maryam
p. 1 - 13
(2016/02/12)

One-Pot Synthesis of N-Monosubstituted Ureas from Nitriles via Tiemann Rearrangement
Amidoximes, obtained from the reaction of nitriles with hydroxylamine, underwent Tiemann rearrangement in the presence of benzenesulfonyl chlorides (TsCl or o-NsCl) to form the N-substituted cyanamides. Subsequently, acidic hydrolysis of the cyanamides afforded the corresponding N-monosubstituted ureas. The synthesis of N-monosubstituted ureas from nitriles was accomplished by three steps in one pot, which provides a direct access to versatile N-monosubstituted urea derivatives from a wide variety of nitriles.
Wang, Chien-Hong,Hsieh, Tsung-Han,Lin, Chia-Chi,Yeh, Wen-Hsiung,Lin, Chih-An,Chien, Tun-Cheng
supporting information
p. 1823 - 1826
(2015/08/06)

4-Dodecylbenzenesulfonic acid (DBSA) promoted solvent-free diversity-oriented synthesis of primary carbamates, S-thiocarbamates and ureas
A simple and highly efficient solvent-free method for the conversion of alcohols, phenols, thiols and amines to primary carbamates, S-thiocarbamates and ureas in the presence of 4-dodecylbenzenesulfonic acid (DBSA) as a cheap and green Bronsted acid reagent has been described. All products were obtained in good to excellent yields and characterized using FT-IR, 1H- and 13C-NMR, MS and CHNS techniques.
Sardarian, Ali Reza,Inaloo, Iman Dindarloo
p. 76626 - 76641
(2015/09/22)

Design and biological evaluation of novel 4-(2-fluorophenoxy)quinoline derivatives bearing an imidazolone moiety as c-Met kinase inhibitors
A series of 4-(2-fluorophenoxy)quinoline derivatives containing an imidazolone moiety were designed, synthesized and evaluated for their in vitro biological activities against c-Met kinase and four cancer cell lines (A549, H460, HT-29 and MKN-45). Most compounds showed moderate to excellent activities in enzyme and cellular assays. The most promising analog, 58 (c-Met IC50 = 1.42 nM), displayed 2.1-, 8.6-fold increase against H460, and MKN-45 cell lines, respectively, compared with foretinib. An analysis of structure-activity relationships revealed that an ortho substituted phenyl ring as well as an N-unsubstituted imidazolone linker is favorable for antitumor activity.
Liao, Weike,Hu, Gang,Guo, Zhuang,Sun, Deyu,Zhang, Lixia,Bu, Yanxin,Li, Yingxiu,Liu, Yajing,Gong, Ping
p. 4410 - 4422
(2015/08/03)

Green synthesis, optical properties and catalytic activity of silver nanoparticles in the synthesis of N-monosubstituted ureas in water
We report the green synthesis of silver nanoparticles by using Euphorbia condylocarpa M. bieb root extract for the synthesis of N-monosubstituted ureas in water. UV-visible studies show the absorption band at 420 nm due to surface plasmon resonance (SPR) of the silver nanoparticles. This reveals the reduction of silver ions (Ag+) to silver (Ago) which indicates the formation of silver nanoparticles (Ag NPs). This method has the advantages of high yields, simple methodology and easy work up.
Nasrollahzadeh, Mahmoud,Babaei, Ferydon,Mohammad Sajadi,Ehsani, Ali
p. 423 - 429
(2014/06/23)

Synthesis of N-arylureas in water and their N-arylation with aryl halides using copper nanoparticles loaded on natural Natrolite zeolite under ligand-free conditions
A new method for the synthesis of N-arylureas and their N-arylation with aryl halides has been developed using copper nanoparticles supported on natural Natrolite zeolite as a reusable heterogeneous catalyst under ligand-free conditions.
Nasrollahzadeh, Mahmoud,Enayati, Mojtaba,Khalaj, Mehdi
p. 26264 - 26270
(2014/07/08)

Selective Synthesis of Mono-substituted Ureas in Low Melting Citric Acid-Urea-Mannitol Mixture
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Mahajan, Hitesh,Bhardwaj, Madhvi,Paul, Satya
p. 463 - 468
(2015/10/28)

Oxidation of phenylthioureas by cetyltrimethylammonium permanganate: A kinetic study
Phenylthioureas have been subjected to oxidation in acetonitrile medium in neutral condition to investigate the oxidation behaviour of cetyltrimethylammonium permanganate on multifunctional groups. The oxidation product in each reaction is found to be the corresponding phenylurea. The rate of reaction is dependent on [CTAP], [phenylthiourea], [surfactant] and reaction temperature. A Michaelis-Menten type kinetics is observed with respect to the substrate. A reaction mechanism involving the formation of a cyclic intermediate in the slow step is proposed for the oxidation reaction.
Sahoo, Prangya Rani,Mishra, Bijay K.
p. 174 - 178
(2014/03/21)

Nano cerium oxide as a recyclable catalyst for the synthesis of N-monosubstituted ureas with the aid of acetaldoxime as an effective water surrogate
A new method for the synthesis of N-monosubstituted ureas has been developed by the reaction of cyanamides with acetaldoxime in the presence of nano cerium oxide as an efficient and recyclable catalyst.
Sajadi, S. Mohammad,Maham, Mehdi
p. 623 - 625
(2013/11/06)

One-pot, solvent-free access to unsymmetrical ureas by palladium-catalysed reductive alkylation using molecular hydrogen
Palladium-catalysed reductive alkylation of monosubstituted ureas has been studied in the presence of aldehydes and using molecular hydrogen as a clean reductant. Unsymmetrical N,N′-disubstituted ureas were formed in good to excellent isolated yields (60-93 %) without the production of salt waste. This reaction was incorporated to a one-pot, solvent-free sequence involving the alkylation of monosubstituted ureas generated in situ from the corresponding amines. Unsymmetrical N,N′-disubstituted ureas were prepared in 60-93 % isolated yield by palladium-catalysed reductive alkylation of monosubstituted ureas using aldehydes as alkylating agents and molecular hydrogen as a clean reductant. A one-pot, solvent-free sequence was also developed from the corresponding amines. Copyright
Mohy El Dine, Tharwat,Chapron, Simon,Duclos, Marie-Christine,Duguet, Nicolas,Popowycz, Florence,Lemaire, Marc
p. 5445 - 5454
(2013/09/02)

Ionic liquid mediated one-pot synthesis of 6-aminouracils
A novel, one-pot synthesis of 6-aminouracils via in situ generated ureas and cyanoacetylureas in the presence of an ionic liquid catalyst, 1,1,3,3-tetramethylguanidine acetate, is described. The catalyst can be recycled for five consecutive runs without loss of activity. The mechanism for the ring closure of cyanoacetylurea to 6-aminouracil is also discussed.
Chavan, Sunil S.,Degani, Mariam S.
supporting information; experimental part
p. 296 - 299
(2012/03/26)

An efficient hydration of cyanamides to substituted ureas with acetaldoxime as an effective water surrogate
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Kim, Sung Hwan,Park, Bo Ram,Kim, Jae Nyoung
scheme or table
p. 716 - 718
(2012/01/06)

Synthesis of novel imidazolidine-2,4-dione derivatives as potential antidiabetic agents
A series of novel imidazolidine-2,4-dione derivatives were synthesized and their chemical structures were confirmed by 1H NMR and ESI-MS. The preliminary antidiabetic screening results demonstrated that the compound 3b showed some antidiabetic activity and could acted as lead compound for further design and discovery of antidiabetic agents.
Cheng, Xian-Chao,Sun, Su-Xia,Zhang, Hao,Dong, Wei-Li,Liu, Gui-You,Wang, Run-Ling,Xu, Wei-Ren
experimental part
p. 4114 - 4116
(2012/01/13)

Design, synthesis, and potential CNS activity of some new bioactive 1-(4-substituted-phenyl)-3-(4-oxo-2-methyl- 4H-quinazolin-3-yl)-urea
Twelve new 1-(4-substituted-phenyl)-3-(4-oxo- 2-methyl-4H-quinazolin-3-yl)- urea were synthesized and screened for anticonvulsant, CNS depressant, and sedativehypnotic activity. After i.p. injection to mice at doses of 30, 100, and 300 mg/kg body weight 2,3-Disubstitutedquinazolin- 4(3H)-one were examined in the maximal electroshock-induced seizures (MES) and subcutaneous pentylenetetrazole (scPTZ) induced seizure models in mice. Spectroscopic data and elemental analysis were consistent with the newly synthesized compounds. The neurotoxicity was assessed using the rotorod method. M3, M4 and M10 were found to be active in both MES screen and scPTZ screen at 0.5 h. All except M11 showed more than 44% decrease in locomotor activity after 1 h of compound administration via actophotometer screen. CNS-depressant activity screened with the help of the forced swim method resulted into some potent compounds. Except for M6 and M11 other tested compounds were found to exhibit potent CNS depressants activity as indicated by increased immobility time. It can be concluded that newly synthesized compounds possessed sedative-hypnotic and CNS depressant activities. Springer Science+Business Media, LLC 2010.
Kashaw, Sushil K.,Kashaw, Varsha,Mishra, Pradeep,Jain,Stables
experimental part
p. 738 - 745
(2012/05/20)

Synthesis of unsymmetrical diarylureas via Pd-catalyzed C-N cross-coupling reactions
A facile synthesis of unsymmetrical N,N′-diarylureas is described. The utilization of the Pd-catalyzed arylation of ureas enables the synthesis of an array of diarylureas in good to excellent yields from benzylurea via a one-pot arylation-deprotection protocol, followed by a second arylation.
Breitler, Simon,Oldenhuis, Nathan J.,Fors, Brett P.,Buchwald, Stephen L.
supporting information; experimental part
p. 3262 - 3265
(2011/08/07)

Microwave-assisted synthesis of N-monosubstituted urea derivatives
An easy and rapid procedure for the preparation of N-monosubstituted ureas via reaction between potassium cyanate and a wide range of amines is described. The procedure was performed under microwave irradiation using water as solvent. This methodology is particularly attractive since it provides ureas in high yield and purity. Georg Thieme Verlag Stuttgart · New York.
De Luca, Lidia,Porcheddu, Andrea,Giacomelli, Giampaolo,Murgia, Irene
scheme or table
p. 2439 - 2442
(2010/11/18)

Synthesis and antitumor evaluation of novel cyclic arylsulfonylureas: ADME-T and pharmacophore prediction
Novel derivatives of 5-(substituted)benzylidene-3-(4-substituted)phenylsulfonylimidazolidine-2,4-diones (3a-r), 1-(4-substituted)phenylsulfonyl-3-(4-substituted)phenylpyrimidine-2,4,6-(1H,3H,5H)-triones (6a-l), and 3-(4-substituted)phenyl-1-(4-substituted)phenylsulfonylquinazoline-2,4(1H,3H)- diones (8a-l) have been synthesized and tested for their antitumor activity against 60 tumor cell lines taken from 9 different organs. The tested compounds have showed good inhibitory effect at the ovarian cancer (IGROV1) cell line. A significant inhibition for (RXF393) renal cancer cells was observed with series 3 compounds, while in the other two series 6 and 8, there was a significant inhibition of ovarian cancer cells (OVCAR-8) and melanoma cells (SK-MEL-2). Interestingly; beside the strong inhibition of compound 3q to IGROV1 and RXF393 cells, a great inhibition (199.62%) for (M14) Melanoma cells was observed at the tested concentration (10?μM). ADME-T and pharmacophore prediction methodology were used to study the antitumor activity of the most active compounds and to identify the structural features required for antitumor activity.
El-Deeb, Ibrahim M.,Bayoumi, Said M.,El-Sherbeny, Magda A.,Abdel-Aziz, Alaa A.-M.
body text
p. 2516 - 2530
(2010/07/05)

Oxidation kinetics of arylthioureas by cetyltrimethylammonium dichromate
Arylthioureas, which are toxic, on oxidation by cetyltrimethylammonium dichromate in acetic acid undergo desulphurization to the corresponding non-toxic arylureas. The mechanism of the oxidation reaction has been studied spectrophotometrically. The rate of reaction is found to be dependent on [CTADC], [phenylthiourea], [acid], [surfactant], polarity of the solvents and reaction temperature. The reaction is fractional order with respect to [substrate] and is catalyzed by acid. With increase in [CTADC], the rate constant decreases. The structure of the substituents has no significant effect on the rate constant. On the basis of various observations, a mechanism has been proposed for the oxidation reaction.
Sahoo, Prangya Rani,Sahu, Sandhyamayee,Patel, Sabita,Mishra
scheme or table
p. 1483 - 1487
(2011/02/28)

Synthesis, anticonvulsant and CNS depressant activity of some new bioactive 1-(4-substituted-phenyl)-3-(4-oxo-2-phenyl/ethyl-4H-quinazolin-3-yl)-urea
Several new 1-(4-substituted-phenyl)-3-(4-oxo-2-phenyl/ethyl-4H-quinazolin-3-yl)-urea were synthesized and screened for anticonvulsant, CNS depressant and sedative-hypnotic activity in the mice. After i.p. injection to mice at doses of 30, 100, and 300 mg/kg body weight synthesized compounds were examined in the maximal electroshock induced seizures (MES) and subcutaneous pentylenetetrazole (scPTZ) induced seizure models in mice. Spectroscopic data and elemental analysis were consistent with the newly synthesized compounds. The neurotoxicity was assessed using the rotorod method. Compounds E1, E6, E9, E12, P3, P4 and P6 were found to be active in the MES screen whereas E1, P4, P6 and P11 were found to be active in the scPTZ screen. All except E6, E11 and P6 showed more than 50% decrease in locomotor activity at 1 h of compound administration via actophotometer screen. CNS depressant activity screened with the help of the forced swim method resulted into some potent compounds. All the compounds were found to exhibit potent CNS depressants activity as indicated by increased immobility time. It can be concluded that newly synthesized compounds possessed promising CNS activities.
Kashaw, Sushil K.,Kashaw, Varsha,Mishra, Pradeep,Jain,Stables
experimental part
p. 4335 - 4343
(2009/12/24)

Synthesis and activity of 1,3,5-triphenylimidazolidine-2,4-diones and 1,3,5-triphenyl-2-thioxoimidazolidin-4-ones: Characterization of new CB 1 cannabinoid receptor inverse agonists/antagonists
Obesity and metabolic syndrome, along with drug dependence (nicotine, alcohol, opiates), are two of the major therapeutic applications for CB 1 cannabinoid receptor antagonists and inverse agonists. In the present study, we report the synthesis and structure-affinity relationships of 1,5-diphenylimidazolidine-2,4-dione and 1,3,5-triphenylimidazolidine-2,4-dione derivatives. These new 1,3,5-triphenylimidazolidine-2,4-dione derivatives and their thio isosteres were obtained by an original pathway and exhibited interesting affinity and selectivity for the human CB1 cannabinoid receptor. A [35S]-GTPγS binding assay revealed the inverse agonist properties of the compounds at the CB1 cannabinoid receptor. Furthermore, molecular modeling studies were conducted in order to delineate the binding mode of this series of derivatives into the CB1 cannabinoid receptor. 1,3-Bis(4-bromophenyl)-5-phenylimidazolidine-2,4-dione (25) and 1,3-bis(4-chlorophenyl)-5-phenylimidazolidine-2,4-dione (23) are the imidazolidine-2,4-dione derivatives possessing the highest affinity for the human CB1 cannabinoid receptor reported to date.
Muccioli, Giulio G.,Wouters, Johan,Charlier, Caroline,Scriba, Gerhard K. E.,Pizza, Teresa,Di Pace, Pierluigi,De Martino, Paolo,Poppitz, Wolfgang,Poupaert, Jacques H.,Lambert, Didier M.
p. 872 - 882
(2007/10/03)

1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives: New templates among the CB1 cannabinoid receptor inverse agonists
New 1-benzhydryl-3-phenylurea derivatives and their 1-benzhydryl-3- phenylthiourea isosteres were synthesized and evaluated for their human CB 1 and CB2 cannabinoid receptor affinity. These compounds proved to be selective CB1 cannabinoid receptor ligands, acting as inverse agonists in a [35S]-GTPγS assay. The affinity of 3,5,5′-triphenylimidazolidine-2,4-dione and 3,5,5′-triphenyl-2- thioxoimidazolidin-4-one derivatives, possessing the 1-benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea moiety, respectively, was also evaluated. In conclusion, the 1-benzhydryl-3-phenylurea scaffold seems to be a new interesting template of CB1 cannabinoid receptor inverse agonists.
Muccioli, Giulio G.,Wouters, Johan,Scriba, Gerhard K. E.,Poppitz, Wolfgang,Poupaert, Jacques H.,Lambert, Didier M.
p. 7486 - 7490
(2007/10/03)

N-aryl N′-hydroxyguanidines, a new class of NO-donors after selective oxidation by nitric oxide synthases: Structure-activity relationship
The formation of nitric oxide (NO) was followed during the oxidation of 37 N-hydroxyguanidines or related derivatives, including 18 new N-aryl N′ -hydroxyguanidines, by recombinant inducible nitric oxide synthase (NOS II). Several N-aryl N′-hydroxyguanidines bearing a relatively small, electron-donating para subtituent, such as H, F, Cl, CH3, OH, OCH3, and NH2, led to NO formation rates between 8 and 41% of that of NO formation from the natural NOS substrate, Nω-hydroxy-L-arginine (NOHA). The characteristics of these reactions were very similar to those previously reported for the oxidation of NOHA by NOS: (i) the strict requirement of NOS containing (6R)-5,6,7,8-tetrahydro-L-biopterin, reduced nicotinamide adenine dinucleotide phosphate, and O2 for the oxidation to occur, (ii) the formation of NO and the corresponding urea in a 1:1 molar ratio, and (iii) a strong inhibitory effect of the classical NOS inhibitors such as Nω-nitro-L-arginine and S-ethyl-iso-thiourea. Structure-activity relationship studies showed that two structural factors are crucial for NO formation from compounds containing a C=NOH function. The first one is the presence of a monosubstituted N-hydroxyguanidine function, since disubstituted N-hydroxyguanidines, amidoximes, ketoximes, and aldoximes failed to produce NO. The second one is the presence of a N-phenyl ring bearing a relatively small, not electron-withdrawing para substituent that could favorably interact with a hydrophobic cavity close to the NOS catalytic site. The kcat value for NOS II-catalyzed oxidation of N-parafluorophenyl N′-hydroxyguanidine was 80% of that found for NOHA, and its kcat/Km value was only 9-fold lower than that of NOHA. Interestingly, the Km value found for NOS II-catalyzed oxidation of N-(3-thienyl) N′-hydroxyguanidine was 25 μM, almost identical to that of NOHA. Recombinant NOS I and NOS III also oxidize several N-aryl N′-hydroxyguanidines with the formation of NO, with a clearly different substrate specificity. The best substrates of the studied series for NOS I and NOS III were N-(para-hydroxyphenyl) and N-(meta-aminophenyl) N′-hydroxyguanidine, respectively. Among the studied compounds, the para-chlorophenyl and paramethylphenyl derivatives were selective substrates of NOS II. These results open the way toward a new class of selective NO donors after in situ oxidation by each NOS family.
Renodon-Cornière, Axelle,Dijols, Sylvie,Perollier, Céline,Lefevre-Groboillot, David,Boucher, Jean-Luc,Attias, Roger,Sari, Marie-Agnes,Stuehr, Dennis,Mansuy, Daniel
p. 944 - 954
(2007/10/03)

Phenylureas. Part 1. Mechanism of the basic hydrolysis of phenylureas
The mechanism of the hydrolytic decomposition of phenylureas in basic media in the pH range 12 to 14 is investigated. In this pH range a levelling of the rate-pH curve is observed as well as a change of the substituent influence on the hydrolysis rate. These experimental findings suggest the formation of an unreactive side product of the phenylurea in a parasitic side equilibrium at sufficiently high pH. The urea dissociates at the aryl-NH group to give its conjugate base. For the hydrolytic decomposition of phenylureas an addition-elimination mechanism is proposed as has been established for the alkaline hydrolysis of carboxylic acid esters and amides.
Laudien,Mitzner
p. 2226 - 2229
(2007/10/03)

REACTION OF BENZAMIDE OXIME DERIVATIVES WITH CHLOROCARBONYLSULFENYL CHLORIDE
Benzamide oxime derivatives (1) were reacted with chlorocarbonylsulfenyl chloride (2) in the presence of a base as a catalyst to afford 3-aryl-4,5-dihydro-1,2,4-thiadiazol-5-one (3), 3-aryl-4,5-dihydro-1,2,4-oxadiazol-5-one (4) and di(benzamide) O,O'-carboxime (5) derivatives in moderate yields.The reaction of N-ethyl-p-toluamide oxime (7) with 2 gave 4-ethyl-4,5-dihydro-3-(p-tolyl)-1,2,4-thiadiazol-5-one (8) and 4-ethyl-4,5-dihydro-3-(p-tolyl)-1,2,4-oxadiazol-5-one (9).
Kawashima, Etsuko,Ando, Yuko,Takada, Toyozo,Tabei, Katsumi
p. 181 - 190
(2007/10/02)

Some Extensions of von Braun (BrCN) Reaction on Organic Bases: Part II
Extensions of von Braun Cyanogen bromide reaction on Ephedra alkaloids and simpler bases have resulted in synthesis of substituted oxazolidines and a whole series of nitrogen analogues of ephedrine, desoxy ephedrine and simpler amines.The general applicability and limitations of such extension of the reaction are also discussed. - Key words: von Braun Cyanogen Bromide Reaction
Malik, Abdul,Afza, Nighat,Siddiqui, Salimuzzaman
p. 512 - 518
(2007/10/02)

Fluorine Containing Bioactive Heterocycles. Part II. Synthesis of Some New Fluorine Containing Arylglyoxals, Their Hydrates and 1,5-Disubstituted Hydantoins
Eight new fluorine containing arylglyoxals have been synthesized by the oxidation of the active methyl group of fluorinated acetophenones by selenium dioxide in dioxan-water medium.The corresponding hydrates were obtained by dissolving arylglyoxals in minimum amounts of benzene and adding hot water.Seventeen new fluorine containing 1,5-disubstituted hydantoins were subsequently prepared by the condensation of these glyoxals with arylureas in ethanol and characterized by ir, pmr and mass spectral studies.Representative compounds have been screened for their possible anticonvulsant and analgesic activities.None of the compounds show significant analgesic activity.
Joshi, Krishna C.,Pathak, Vijai N.,Goyal, Mahendra K.
p. 1651 - 1653
(2007/10/02)