статьи / ᯨ᮪

• Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics

Volume 1647, Issues 1–2, 11 April 2003, Pages 193–199

Physiological and pathological implications of semicarbazide-sensitive amine oxidase

Peter H Yu, , Shannon Wright, Ellen H Fan, Zhao-Rong Lun, Diana Gubisne-Harberle

Abstract

Semicarbazide-sensitive amine oxidase (SSAO) catalyzes the deamination of primary amines. Such deamination has been shown capable of regulating glucose transport in adipose cells. It has been independently discovered that the primary structure of vascular adhesion protein-1 (VAP-1) is identical to SSAO. VAP-1 regulates leukocyte migration and is related to inflammation. Increased serum SSAO activities have been found in patients with diabetic mellitus, vascular disorders and Alzheimer's disease. The SSAO-catalyzed deamination of endogenous substrates, that is, methylamine and aminoacetone, led to production of toxic formaldehyde and methylglyoxal, hydrogen peroxide and ammonia, respectively. These highly reactive aldehydes have been shown to initiate protein cross-linkage, exacerbate advanced glycation of proteins and cause endothelial injury. Hydrogen peroxide contributes to oxidative stress. ¹⁴C-methylamine is converted to ¹⁴C-formaldehyde, which then forms labeled long-lasting protein adduct in rodents. Chronic methylamine treatment increased the excretion of malondialdehyde and microalbuminuria, and enhanced the formation of fatty streaks in C57BL/6 mice fed with an atherogenic diet. Treatment with selective SSAO inhibitor reduces atherogenesis in KKAy diabetic mice fed with high-cholesterol diet. Aminoguanidine, which blocks advanced glycation and reduces nephropathy in animals, is in fact more potent at inhibiting SSAO than its effect on glycation. It suggests that SSAO is involved in vascular disorders under certain pathological conditions. Although SSAO has been known for several decades, its physiological and pathological implications are just beginning to be recognized.

• Tetrahedron Letters

Volume 47, Issue 49, 4 December 2006, Pages 8651–8652

Urea nitrate and nitrourea: powerful and regioselective aromatic nitration agents

Joseph Almoga, , , Asne Kleina, Anat Sokola, Yoel Sassona, Dana Sonenfeldb, Tsippy Tamirib

Abstract

Urea nitrate (UN) and nitrourea (NU), easily prepared from urea and nitric acid, convert deactivated aromatic compounds to the corresponding nitrated derivatives with a high yield and a high regioselectivity under very mild conditions. The performance of the two reagents is quite similar indicating that NU is an intermediate in the UN nitration process.

• Russian Journal of General Chemistry

November 2006, Volume 76, Issue 11, pp 1719-1723

Synthesis and properties of Fe(II), Ni(II), Co(II), and Zn(II) chelates with 4-nitrosemicarbazide

S. G. Il’yasov, A. A. Lobanova, N. I. Popov, I. V. Kazantsev, V. L. Varand, S. V. Larionov

Abstract

Chelates M(O₂NNCONHNH₂)₂ · 2H₂O (M = Fe, Co, Ni, Zn) were prepared by the reactions of 4-nitrosemicarbazide with appropriate 3d transition metal salts. The structures of the compounds were suggested on the basis of data obtained by physicochemical methods. The compounds obtained were shown to be energetic substances.

• Russian Journal of Organic Chemistry

December 2002, Volume 38, Issue 12, pp 1731-1738

Chemistry of Urea Nitro Derivatives: III. Reactions of N,N'-Dinitrourea with Bases

S. G. Il'yasov, A. A. Lobanova, N. I. Popov, R. R. Sataev

Abstract

N,N'-Dinitrourea reacts with bases to form the corresponding acid or neutral salts. Its reaction with hydrazine yields 4-nitrosemicarbazide, and the reaction with hydroxylamine leads to N-hydroxy-N'-nitrourea.

• Propellants, Explosives, Pyrotechnics

Volume 38, Issue 3, pages 327–334, June 2013

Synthesis, Structure, and Properties of N,N′-Dinitrourea

Sergey G. Il'yasov1,*, Gennady V. Sakovich1 andAntonina A. Lobanova2

Abstract

Information on synthesis methods and properties of N,N′-dinitrourea and its salts, which were reported virtually simultaneously by different authors in different publications, is summarized and systematized. Merits and drawbacks of various approaches for the synthesis of the target products are discussed. The reactivity of N,N′-dinitrourea and its salts in the reactions of nucleophilic substitution and condensation is discussed.

• Letters in Organic Chemistry, Volume 7, Number 3, April 2010, pp. 249-254(6)

Metal-Free Oxidation of Urazole and 1,4-Dihydropyridine Derivatives Under Mild and Heterogeneous Conditions by Nitro Urea, Derived from Urea Nitrate, and Silica Sulfuric Acid

Authors: Ghorbani-Choghamarani, Arash; A. Zolfigol, Mohammad; Hajjami, Maryam; Rastgoo, Shahrbanoo; Mallakpour, Shadpour

Abstract:

Mild combination of nitro urea, derived from urea nitrate, and silica sulfuric acid (SiO2OSO3H) might act as an efficient oxidizing media, which could be able to oxidize different types of heterocyclic compounds including urazoles and 1,4-dihydropyridines. The process presented here is operationally simple, environmentally benign, and reactions have been mildly carried out in dichloromethane at room temperature. 

• Tetrahedron

Volume 60, Issue 44, 25 October 2004, Pages 9953–9961

Reaction of 3-aminoquinoline-2,4-diones with nitrourea. Synthetic route to novel 3-ureidoquinoline-2,4-diones and imidazo[4,5-c]quinoline-2,4-diones

Antonín Kláseka, , , Antonín Lyčkab, Michal Holčapekc, Ignác Hozaa

Abstract

1-Unsubstituted 3-alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diones react with 1-substituted and 1,1-disubstituted ureas in boiling acetic acid to give 2,6-dihydro-imidazo[1,5-c]quinazoline-3,5-diones. In contrast, the reaction of these amines with nitrourea in dioxane affords novel 3-alkyl/aryl-3-ureido-1H,3H-quinoline-2,4-diones or 9b-hydroxy-3a-alkyl/aryl-3,3a,5,9b-tetrahydro-1H-imidazo[4,5-c]quinoline-2,4-diones, which can smoothly be dehydrated to 3a-alkyl/aryl-3,3a-dihydro-5H-imidazo[4,5-c]quinoline-2,4-diones. All three types of products can be converted to 2,6-dihydro-imidazo[1,5-c]quinazoline-3,5-diones by refluxing in acetic acid.

• Journal of heterocyclic chemistry

2006, vol. 43, no5, pp. 1251-1260 [10 page(s) (article)]

Molecular rearrangement of 1-substituted 3-aminoquinoline-2,4-diones in their reaction with urea and nitrourea synthesis and transformations of reaction intermediates

KLASEK Antonin ; LYCKA Antonin ; HOLCAPEK Michal ; KOVAR Michal ; HOZA Ignac

• Chemical Journal of Chinese Universities》 2010-12Add to Favorite Get Latest Update

3D-QSAR Study of N-Nitro Urea Derivatives with Herbicidal Activity

SHEN Xiao-Xia,XU Sheng-Zhen,CHEN Chang-Shui(Department of Chemistry,College of Science,Huazhong Agricultural University,Wuhan 430070,China)

Urea derivatives have occupied a pivotal position in pesticide chemistry due to their significant activities,including herbicidal activities,antimicrobial and so on.And N-nitro substituted anilines also displayed herbicidal properties.So we proposed that urea derivatives bearing a new group nitro in the NH—CO—NH bridge should display some interesting fungicidal activities.The preliminary bioassays indicated that N-nitro urea derivatives possess good activity against A.retroflexus L and S.sudanenses.To design the highly active title compounds,comparative molecular field analysis(CoMFA) was applied to the study of the three-dimensional quantitative structure activity relationship(3D-QSAR) on 38 N-nitro urea derivatives.The reasonable models with predictive ability were obtained from the investigation(A.retroflexus L:q2=0.674,r2=1.000,R2pred=0.9989;S.sudanenses:q2=0.635,r2=1.000,R2pred=0.9958).The steric and electronic contour maps show that bulky and electropositive groups linked to 2-,5-position of N'-phenyl ring,electronegetive groups to 3-position,small and electronegetive groups to 4-,6-position may increase the herbicidal activity against A.retroflexus L,and also bulky and electronegetive groups to 2-position,small and electronegetive groups to 3-position,bulky and electropositive groups to 4-position,bulky groups to 5-position may increase the activity against S.sudanenses.

• Chinese Journal of Chemistry

Volume 29, Issue 4, pages 731–734, April, 2011

A Mild Procedure for the Preparation of o-Nitrophenols by Nitro Urea or Ammonium Nitrate in the Presence of Silica Sulfuric Acid (SiO2-OSO3H)

Arash Ghorbani-Choghamarani*, Mohsen Nikoorazm, Hamid Goudarziafshar, Zahra Naserifar andParisa Zamani

Abstract

A mixture of ammonium nitrate or nitro urea and silica sulfuric acid was found to be efficient and environmentally friendly nitrating media for the preparation of orto-nitro phenols in dichloromethane at room temperature.

• Journal of Energetic Materials

Volume 26, Issue 3, 2008

A Theoretical Study on Nitrourea and its Tautomers

Abstract

In the present study, nitrourea and its possible tautomers have been subjected to theoretical analysis by performing Hartree-Fock and also density functional theory (DFT) calculations. The optimized geometries, vibrational frequencies, and some thermodynamical values for the presently considered species have been obtained in their ground states.

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