cas 2158-03-4, 1-CARBAMYLPIPERIDINE | Articles data

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Sequential base-promoted annulation/palladium-catalyzed domino 1,5-enyne arylation and vinylation of α-propargylaminohydrazones
Stereoselective dominos: Cascade reactions of easily accessible α-propargylaminohydrazones 1 represent a simple and efficient method for the preparation of pyrazolones 3.
Rossi, Elisabetta,Arcadi, Antonio,Abbiati, Giorgio,Attanasi, Orazio A.,De Crescentini, Lucia
p. 1400 - 1402
(2002)
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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)

Regioselective Formal [3+2] Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation
A new class of intermolecular olefin aminooxygenation reaction is described. This reaction utilizes the classic halonium intermediate as a regio- and stereochemical template to accomplish the selective oxyamination of both activated and unactivated alkenes. Notably, urea chemical feedstock can be directly introduced as the N and O source and a simple iodide salt can be utilized as the catalyst. This formal [3+2] cycloaddition process provides a highly modular entry to a range of useful heterocyclic products with excellent selectivity and functional-group tolerance.
Wu, Fan,Alom, Nur-E,Ariyarathna, Jeewani P.,Na?, Johannes,Li, Wei
supporting information
p. 11676 - 11680
(2019/07/31)

A Physical Organic Approach to Tuning Reagents for Selective and Stable Methionine Bioconjugation
We report a data-driven, physical organic approach to the development of new methionine-selective bioconjugation reagents with tunable adduct stabilities. Statistical modeling of structural features described by intrinsic physical organic parameters was applied to the development of a predictive model and to gain insight into features driving the stability of adducts formed from the chemoselective coupling of oxaziridine and methionine thioether partners through Redox Activated Chemical Tagging (ReACT). From these analyses, a correlation between sulfimide stabilities and sulfimide ν (C=O) stretching frequencies was revealed. We exploited the rational gains in adduct stability exposed by this analysis to achieve the design and synthesis of a bis-oxaziridine reagent for peptide stapling. Indeed, we observed that a macrocyclic peptide formed by ReACT stapling at methionine exhibited improved uptake into live cells compared to an unstapled congener, highlighting the potential utility of this unique chemical tool for thioether modification. This work provides a template for the broader use of data-driven approaches to bioconjugation chemistry and other chemical biology applications.
Christian, Alec H.,Jia, Shang,Cao, Wendy,Zhang, Patricia,Meza, Arismel Tena,Sigman, Matthew S.,Chang, Christopher J.,Toste, F. Dean
supporting information
p. 12657 - 12662
(2019/09/04)

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)

N - amino piperidine hydrochloride preparation method
The invention relates to a preparation method of N-aminopiperidine hydrochloride. The preparation method comprises the steps: mixing piperidine with urea, and performing heating reflux reaction for 2-8 hours to obtain N-formamide piperidine; introducing chlorine gas for reaction for 1-2.5 hours when the dissolved N-formamide piperidine is at 0-20 DEG C, then carrying out Hoffmann rearrangement reaction under an alkaline condition to obtain N-aminopiperidine, reacting N-aminopiperidine with concentrated hydrochloric acid to obtain N-aminopiperidine hydrochloride. According to the preparation method of N-aminopiperidine hydrochloride, urea which serves as a raw material is low in cost and easy to obtain, highly toxic compounds such as hydrazine hydrate are not used, and nitro compounds with strong carcinogenicity are not produced in a synthetic process; and reaction conditions are mild, operation is simple, after-treatment is simple and convenient, and reaction yield is high.
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Paragraph 0027; 0028; 0029

(2017/08/25)

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)

Transamidation of carboxamides catalyzed by Fe(III) and water
The highly efficient transamidation of several primary, secondary, and tertiary amides with aliphatic and aromatic amines (primary and secondary) is described. The reaction is performed in the presence of a 5 mol % concentration of different hydrated salts of Fe(III), and the results show that the presence of water is crucial. The methodology was also applied to urea and phthalimide to demonstrate its versatility and wide substrate scope. An example of its use is an intramolecular application in the synthesis of 2,3-dihydro-5H-benzo[b]-1,4- thiazepin-4-one, which is the bicyclic core of diltiazem and structurally related drugs (Budriesi, R.; Cosimelli, B.; Ioan, P.; Carosati, E.; Ugenti, M. P.; Spisani, R. Curr. Med. Chem. 2007, 14, 279-287). A plausible mechanism that explains the role of water is proposed on the basis of experimental observations and previous mechanistic suggestions for transamidation reactions catalyzed by transition metals such as copper and aluminum. This methodology represents a significant improvement over other existing methods; it can be performed in air and with wet or technical grade solvents.
Becerra-Figueroa, Liliana,Ojeda-Porras, Andrea,Gamba-Sánchez, Diego
p. 4544 - 4552
(2014/06/09)

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.
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(2010/03/02)

Five-membered heterocyclic compounds as inhibitors of SRC family protein kinase.
The present invention refers to novel substituted aromatic heteroaryl derivatives of formula (I). with the definitions of A, L1, L2, G, J, X and Y according to claim 1. These novel compounds are useful for the inhibition of protein kinases, particularly of the inhibition of Src family protein kinases. Methods for inhibiting kinases by contacting kinases with these novel compounds are disclosed. In another embodiment the present invention refers to pharmaceutical compositions containing these novel compounds and their use for the preparation of medicaments for treating diseases or disorders associated with unphysiological activity of kinases in the body, particularly for the treatment of cancer, immunosuppression, and osteoporosis.
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Page/Page column 15

(2008/06/13)

CCR5 antagonists useful for treating AIDS
Compounds of the formula 1or a pharmaceutically acceptable salt or isomer thereof, wherein: Q, X and Z are CH or N; R, R4-R7 and R13 are H or alkyl; R1 is H, alkyl, fluoroalkyl, R9-arylalkyl, R9-heteroarylalkyl, alkyl—SO2—, cycloalkyl—SO2—, fluoroalkyl—SO2—, R9-aryl—SO2—, R9-heteroaryl—SO2—, N(R22)(R23)—SO2—, alkyl—C(O)—, cycloalkyl—C(O)—, fluoroalkyl—C(O)—, R9-aryl—C(O)—, NH-alkyl—C(O)— or R9-aryl—NH—C(O)—; R2 is H and R3 is H, alkyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, R9-aryl, R9-arylalkyl, R9-heteroaryl, or R9-heteroarylalkyl, and when X and Z are each CH, R3 is alkoxy, R9-aryloxy, R9-heteroaryloxy, alkylC(O)O—, alkylaminoC(O)O—, alkylOC(O)NR13—, alkylOC(O)NR13— or alkylaminoC(O)NR13—; or R2 and R3 together are =O, =NOR10, =N—NR11R12 or =CH-alkyl; R8 is substituted phenyl, substituted heteroaryl, naphthyl, fluorenyl, diphenymethyl, alpha-substituted benzyl or alpha-substituted heteroarylmethyl; R9-R12 are as defined; are disclosed for the treatment of HIV, solid organ transplant rejection, graft v. host disease, inflammatory diseases, atopic dermatitis, asthma, allergies or multiple sclerosis, as well as pharmaceutical compositions and combinations with antiviral or anti-inflammatory agents.
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(2008/06/13)

A simple conversion of amines into monosubstituted ureas in organic and aqueous solvents
A versatile and highly efficient synthesis of monosubstituted ureas is described. The reaction of an amine with 4-nitrophenyl-N-benzylcarbamate, followed by hydrogenolysis, provides the corresponding urea in high yield and purity. This carbamate can also be employed for the derivatization of water-soluble polyamines (e.g. aminoglycoside antibiotics), while other reagents (e.g. benzylisocyanate) fail to give the desired products in any significant yield.
Liu, Qi,Luedtke, Nathan W.,Tor, Yitzhak
p. 1445 - 1447
(2007/10/03)

1-amino-7-isoquinoline derivatives as serine protease inhibitors
The invention relates to serine protease inhibitor compounds of fornula (I) where R1is hydrogen, halo, cyano, nitro or hydroxyl, amino, alkoxy, alkyl amminoalkyl, hydroxyalkyl, thiol, alkylthio, aminosulphonyl alkoxyalkyl, alkoxycarbonyl, acyloxymethoxycabonyl or alkylamino optionally substituted by hydroxy, alkylamino, alkoxy, oxo, aryl, cycloalkyl, amino, halo, cyano, nitro, thiol, alkylthio, alkylsulphonyl, alkylsulphenyl, alkylsulphonamido, alkylaminosulphonyl, haloalkoxy and haloalkyl; R2is hydrogen, halo, methyl amino, hydroxy, or oxo; and R is X—X—Y(R7)—L—Lp(D)n; wheren each X independently is a C, N, O or S atom or a CO, CR1, C(R1)2or NR1group, at least one X being C, CO, CR1or a C(R1)2group; Y (the α-atom) is a nitrogen atom or a CR1group or Y and L taken together form a cyclic group; R7is a lipophilic group selected from alkyl, alkenyl, mono- or bi-cycloalkyl, aryl, heteroaryl, mono- or bicycloalkylalkyl, mono- or bicycloalkylakenyl, aralkyl, heteroaryl-alkyl, arylalkenyl, heteroarylalkenyl all optionally substituted by a group R1; L is an organic linker group containing 1 to 5 backbone atoms selected from C, N, O and S, or a branched alkyl or cyclic group; Lp is a lipophilic organic group selected from alkyl, heterocyclic, alkenyl, alkaryl cycloalkyl, polycycloalkyl, cycloalkenyl, aryl, aralkyl or haloalkyl group or a combination of two or more such groups optionally substituted by one or more of oxa, thia, aza or R1groups; D is a hydrogen bond donor group; and n is 0, 1 or 2 and salts thereof.
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(2008/06/13)

Oxidative cleavage of the C=N bond during singlet oxygenations of amidoximates
Amidoximes are inert toward singlet oxygen (1O2), however, the photooxygenation of amidoximate anions proceeds smoothly and in high yield to give mixtures of amides and nitriles. The mechanism of these reactions appears to involve carbonyl oxide intermediates. The oxidative cleavage of amidoximates closely resembles the results obtained from nitric oxide synthase (NOS) oxidations of N-hydroxyarginine.
?cal, Nüket,Erden, Ihsan
p. 4765 - 4767
(2007/10/03)

Metalloporphyrin catalyzed oxidation of N-hydroxyguanidines: A biomimetic model for the H2O2-dependent activity of nitric oxide synthase
A chemical model for the H2O2 promoted oxidation by nitric oxide synthase (NOS) has been developed. Biomimetic oxidations were carried out using H2O2 and tetrakis(perfluorophenyl)porphyrinato-iron(III) chloride (FeTPPF20) as a catalyst. Similarly to NOS our model system produces N(δ)-cyanoornithine, citrulline and NO from NOHA and did not oxidize arginine itself. Based on these results we propose a peroxide shunt to be involved in the catalytic cycle of NOS. To the best of our knowledge this is the first chemical system that semiquantitatively mimics NOS activity. (C) 2000 Elsevier Science Ltd. All rights reserved.
Keseru, Gyoergy M.,Balogh, Gyoergy T.,Karancsi, Tamas
p. 1775 - 1777
(2007/10/03)

Preparation of 1-substituted-4-phenylpiperidines as central nervous system agents.
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(2008/06/13)

Peracid oxidation of an N-hydroxyguanidine compound: A chemical model for the oxidation of N(ω)-hydroxy-L-arginine by nitric oxide synthase
Arginine is oxidized by a class of enzymes called the nitric oxide synthases (NOS) to generate citrulline and, presumably, nitric oxide (·NO). N-Hydroxylation of a guanidinium nitrogen of arginine to generate N- hydroxyarginine (NOHA) has been shown to be a step in the biosynthesis of ·NO. In an effort to elucidate the mechanism by which further oxidation of NOHA occurs, the oxidation of a model N-hydroxyguanidine compound by several peracids was studied in depth. This oxidative chemistry is a possible model for the enzymatic process since the corresponding urea (or citrulline equivalent product) is obtained along with an oxidized nitrogen species. The oxidized nitrogen product was, however, not ·NO but rather HNO. ·NO generation in this chemical system and in the enzymatic process would require another one-electron oxidation. The mechanistic details of this are further discussed.
Fukuto,Stuehr,Feldman,Bova,Wong
p. 2666 - 2670
(2007/10/02)

Mercapto-acylamino acid antihypertensives
Novel mercapto-acylamino acids useful in the treatment of hypertension and combinations of mercapto-acylamino acids and atrial natriuretic factors or angiotensin converting enzyme inhibitors useful for treating hypertension are disclosed.
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(2008/06/13)

Mercapto-acylamino acid antihypertensives
Novel mercapto-acylamino acids useful in the treatment of hypertension and combinations of mercapto-acylamino acids and atrial natriuretic factors or angiotensin converting enzyme inhibitors useful for treating hypertension are disclosed.
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(2008/06/13)

Synthesis of substituted urea compounds
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Henklein,Jahrling,Teubner,Tietze,Ott
p. 225 - 226
(2007/10/02)

Antihypertensive cyanoguanidines
This invention relates to novel tri-substituted guanidines linked to a piperidine ring. More specifically, it relates to cyanoguanidines of formula I STR1 wherein R1, R2, R3, R4 are substituents n is an integer of zero to 1 n' is an integer of zero to 1 A and B are --CH2 --, CHOH, --CO-- or a single bond as well as the acid addition salts thereof with a mineral or organic acid. The compounds have interesting pharmacological properties which make them useful as active ingredient of medicines, e.g. antihypertensives.
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(2008/06/13)

OXIDATION OF AZACYCLOALKANES
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Troyanskii, E. I.,Ioffe, V. A.,Nikishin, G. I.
p. 2351 - 2359
(2007/10/02)

Some Extensions of von Braun (BrCN) Reaction on Organic Bases, Part IV
Extensions of von Braun cyanogen bromide reaction have been undertaken on some aliphatic and heterocyclic amines.Monocyanamides of all these bases yielded their respective urea and carboxamide derivatives on hydrolysis with dilute hydrochloric acid.They also gave the amido derivatives on reaction with Zn/HCl, as in the case of diisobutyl and di-2-butyl cyanamides. - Key words: von Braun Cyanogen Bromide Reaction
Siddiqui, Salimuzzaman,Haider, S. Imtiaz,Ahmad, S. Salman,Siddiqui, B. Shaheen
p. 546 - 549
(2007/10/02)

An efficient synthesis of 1,1-disubstituted hydrazines
1,1-disubstituted hydrazines were prepared from the corresponding 1,1-disubstituted ureas by means of the Hofmann rearrangement reaction. The yields were fairly good, except from the ureas susceptible to oxidation, and thus the present method represents an additional and efficient procedure for the synthesis of 1,1-disubstituted hydrazines.
Murakami,Yokoyama,Sasakura,Tamagawa
p. 423 - 428
(2007/10/02)

HYDROGEN BONDED COMPLEXES IV; UREA-PHENOL COMPLEXES
A number of crystalline, hydrogen-bonded complexes of ureas and phenols are reported.The most commonly observed urea-phenol ratio is 1:1, but some complexes with ratios of 2:1, 1:2 and 1:3 were encountered.The structures of these complexes are discussed and one degradative reaction is described.
Barry, John E.,Finkelstein, Manuel,Hutchins, Gudrun A.,Ross, Sidney D.
p. 2151 - 2156
(2007/10/02)

REACTIONS OF ORGANIC THIOCYANATES WITH NUCLEOPHILIC REAGENTS. III. SYNTHESIS OF SUBSTITUTED CYANAMIDES FROM THIOCYANATES AND AMINES
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Rybin, A. G.,Zil'berman, E. N.,Trachenko, V. I.,Sotnik, A. N.
p. 1606 - 1607
(2007/10/02)

Organic compounds substituted heptadeca-5,9- and 5,10-dienoic acid
The present invention provides novel substituted heptadeca-5,9- and 5,10-dienoic acid and similar fatty acid compounds which are derivatives of certain prostaglandins and are potent thromboxane A2 inhibitors. By virtue of this pharmacological property, they represent useful pharmacological agents for a wide variety of purposes.
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(2008/06/13)

Conformational Preferences in Alkylnitrosoureas
The spectroscopic properties of several N-alkyl-N-nitrosoureas, N,N'-dialkyl-N-nitrosoureas, and N,N',N'-trialkyl-N-nitrosoureas have been studied in carbon disulfide and chloroform solutions.The NH stretching frequencies in the IR spectra have been observed in both concentrated and dilute solution and in the presence of added dioxane.The results indicate that there is a strong intramolecular hydrogen bond in the mono- and dialkylnitrosoureas.The chemical shifts and line widths of the NMR spectra have also been studied in these solvents.The large chemical shift differences, about 1.3 ppm, for the NH protons in the monoalkylnitrosoureas and other spectroscopic features in the monoalkyl- and dialkylnitrosoureas also indicate that an intramolecular hydrogen bond contributes to a strong conformational preference.The temperature dependence of the NMR spectra of several N,N',N'-trialkyl-N-nitrosoureas establishes that the energy barrier for rotation about the carbon dialkylamide bond is about 13 kcal mol-1.Dipolar resonance interactions are primarily responsible for this barrier.This interaction is augmented by a strong, 8-10 kcal mol-1, hydrogen bond in the mono- and dialkylnitrosoureas.
Snyder, John K.,Stock, Leon M.
p. 886 - 891
(2007/10/02)

Cycloamides of nitriloprostacyclins
This invention relates to certain structural and pharmacological analogs of prostacyclin (PGI2) wherein a nitrogen atom is substituted for the 6,9α-epoxy-oxygen of prostacyclin. These novel nitrogen-containing prostacyclin-type compounds are useful for the pharmacological purposes for which prostacyclin is used, e.g., as antithrombotic agents, antihypertensive agents, antiasthma agents, nasal decongestants, or regulators of fertility and procreation.
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(2008/06/13)

Inter-phenylene-PG amides
The present invention relates to novel amido, cycloamido, carbonylamido, sulfonylamido, and hydrazino derivatives of inter-phenylene-PG-type compounds. These novel derivatives produce surprisingly prolonged oral activity, particularly as anti-thrombotic agents, as compared to the previously known inter-phenylene-PG-type acids and esters.
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(2008/06/13)