cas 827-41-8, 5-AMINO-3-PHENYLPYRAZOLE | Articles data

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NIS-promoted three-component reaction of 3-oxo-3-arylpropanenitriles with arylsulfonyl hydrazides
A new three-component reaction of 3-oxo-3-arylpropanenitriles with arylsulfonyl hydrazides has been established, and an expanded inventory of 3-aryl-4-(arylthio)-1H-pyrazol-5-amines is synthesized by sequential cyclization and sulfenylation reactions under the action of NIS. In addition to the attractive features of multicomponent reactions, the protocol presents broad substrate scope, good functional group tolerance and mild reaction conditions. The utility of this procedure is further established by gram-scale synthesis as well as the diversified transformations of the products to useful compounds. This journal is
Wei, Yueting,Liu, Ping,Liu, Yali,He, Jing,Li, Xuezhen,Li, Shiwu,Zhao, Jixing
p. 3932 - 3939
(2021/05/14)

2-pyridine substituted urea structural small molecule compounds as well as synthesis and application thereof
The invention relates to 2-pyridine substituted urea structural small molecule compounds as well as synthesis and application thereof. Specifically, the invention discloses the compounds represented by a formula (I) shown in the specification, enantiomers, diastereomers, racemates or a mixture of the compounds, or a pharmaceutically acceptable salt, hydrate and solvate of the compounds, a preparation method of the above materials, and applications of the above materials in preparation of an ASK1 small molecule inhibitor, or medicines for preventing and/or treating diseases related to ASK1, especially liver diseases, lung diseases, cardiovascular diseases, kidney diseases and metabolic diseases.
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Paragraph 0197; 0626-0628

(2020/03/03)

Synthesis and biological evaluation of 7-(aminoalkyl)pyrazolo[1,5-a]pyrimidine derivatives as cathepsin K inhibitors
A series of novel 7-aminoalkyl substituted pyrazolo[1,5-a]pyrimidine derivatives were synthesized and tested for inhibition of cathepsin K. The synthetic methodology comprises cyclization of 5-aminopyrazoles with N-Boc-α-amino acid-derived ynones followed by transformation of the ester and the Boc-amino functions. It allows for easy diversification of the pyrazolo[1,5-a]pyrimidine scaffold at various positions. Molecular docking studies with pyrazolo[1,5-a]pyrimidine derivatives were also performed to elucidate the binding mode in the active site of cathepsin K. The synthesized compounds exhibited moderate inhibition activity (Ki ≥ 77 μM).
Petek, Nejc,?tefane, Bogdan,Novinec, Marko,Svete, Jurij
p. 226 - 238
(2018/12/04)

Synthesis of pyrazolopyrimidinones using a “one-pot” approach under microwave irradiation
A simple one-pot method for the microwave-assisted synthesis of substituted pyrazolo[1,5-a]pyrimidinones, a core scaffold in many bioactive and pharmaceutically relevant compounds, has been established. A variety of substituents was tolerated at the 2 and 5 positions, including functionalized aryls, heterocycles, and alkyl groups.
Kelada, Mark,Walsh, John M. D.,Devine, Robert W.,McArdle, Patrick,Stephens, John C.
supporting information
p. 122 - 1228
(2018/06/13)

Molecular docking design and one-pot expeditious synthesis of novel 2,5-diarylpyrazolo[1,5-a]pyrimidin-7-amines as anti-inflammatory agents
Abstract A series of novel 2,5-diarylpyrazolo[1,5-a]pyrimidin-7-amines were designed as COX-2 inhibitors by molecular docking studies and their synthesis was accomplished via an expeditious one-pot reaction. Structures of the compounds were established by
Aggarwal, Ranjana,Singh, Gulshan,Kaushik, Pawan,Kaushik, Dhirender,Paliwal, Deepika,Kumar, Ajay
p. 326 - 333
(2015/07/15)

Direct synthesis of pyrazoles from esters using tert-butoxide-assisted C-(C=O) coupling
This paper describes the direct synthesis of pyrazoles from esters that comprises two sequential reactions: tert-butoxide-assisted C-C(=O) coupling reaction to yield β-ketonitrile or α,β-alkynone intermediates, and condensation by hydrazine addition. The method reported allows for easy control of the regioselectivity and structure of substituents at N-1, C-3, C-4 and/or C-5 positions.
Kim, Bo Ram,Sung, Gi Hyeon,Ryu, Ki Eun,Lee, Sang-Gyeong,Yoon, Hyo Jae,Shin, Dong-Soo,Yoon, Yong-Jin
p. 9201 - 9204
(2015/06/08)

Structure-activity relationship studies of SEN12333 analogues: Determination of the optimal requirements for binding affinities at α7 nAChRs through incorporation of known structural motifs
Alpha7 nicotinic acetylcholine receptors (nAChRs) have implications in the regulation of cognitive processes such as memory and attention and have been identified as a promising therapeutic target for the treatment of the cognitive deficits associated with schizophrenia and Alzheimer's disease (AD). Structure affinity relationship studies of the previously described α7 agonist SEN12333 (8), have resulted in the identification of compound 45, a potent and selective agonist of the α7 nAChR with enhanced affinity and improved physicochemical properties over the parent compound (SEN12333, 8).
Beinat, Corinne,Reekie, Tristan,Banister, Samuel D.,O'Brien-Brown, James,Xie, Teresa,Olson, Thao T.,Xiao, Yingxian,Harvey, Andrew,O'Connor, Susan,Coles, Carolyn,Grishin, Anton,Kolesik, Peter,Tsanaktsidis, John,Kassiou, Michael
p. 277 - 301
(2015/03/31)

Pyrazolotriazines as inhibitors of nucleases
The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3 and R4 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.
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Paragraph 0122; 0123; 0124; 0125; 0126; 0127; 0134-0138

(2016/01/12)

Discovery of mixed type thymidine phosphorylase inhibitors endowed with antiangiogenic properties: Synthesis, pharmacological evaluation and molecular docking study of 2-thioxo-pyrazolo[1,5-a][1,3,5]triazin-4-ones. Part II
In our drug discovery program, a series of 2-thioxo-pyrazolo[1,5-a][1,3,5] triazin-4-ones were designed, synthesized and evaluated for their TP inhibitory potential. All the synthesized analogues conferred a varying degree of TP inhibitory activity, comparable or better than positive control, 7-deazaxanthine (7-DX, 2) (IC50 value = 42.63 μM). A systematic approach to the lead optimization identified compounds 3c and 4a as the most promising TP inhibitors, exhibiting mixed mode of enzyme inhibition. Moreover, selected compounds demonstrated the ability to attenuate the expression of the angiogenic markers (viz. MMP-9 and VEGF) in MDA-MB-231 cells at sublethal concentrations. In addition, molecular docking studies revealed the plausible binding orientation of these inhibitors towards TP, which was in accordance with the experimental results. Taken as a whole, these compounds would constitute a new direction for the design of novel TP inhibitors with promising antiangiogenic properties.
Bera, Hriday,Ojha, Probir Kumar,Tan, Bee Jen,Sun, Lingyi,Dolzhenko, Anton V.,Chui, Wai-Keung,Chiu, Gigi Ngar Chee
p. 294 - 303
(2014/04/17)

A new, one-pot, multicomponent synthesis of 5-aza-9-deaza-adenines under microwave irradiation
A new, practical, three-component method for the synthesis of 5-aza-9-deaza-adenines is developed. Aminopyrazoles react in a one-pot fashion with triethyl orthoformate and cyanamide under microwave irradiation affording 5-aza-9-deaza-adenines in good yiel
Lim, Felicia Phei Lin,Luna, Giuseppe,Dolzhenko, Anton V.
p. 5159 - 5163
(2014/12/10)

A convenient synthesis of 3- and 5-amino-1 H -pyrazoles via 3(5)-amino-4-(ethylsulfi nyl)-1 H -pyrazole desulfi nylation
Syntheses of 5-amino-3-aryl- and 3-amino-5-aryl-1 H -pyrazoles from β -bromo- α -(ethylsulfanyl)cinnamonitrile are described. The β -bromo- α -(ethylsulfanyl)cinnamonitriles were oxidized with H2O 2 to the corresponding β -bromo- α -
Lassagne, Frederic,Snegaroff, Katia,Roisnel, Thierry,Nassar, Ekhlass,Mongin, Florence
p. 139 - 145
(2011/12/01)

Synthesis of pyrazolo[5,1-d][1,2,3,5]tetrazine-4(3H)-ones
A solid-phase synthesis of 5-aminopyrazole has been developed and applied to the preparation of pyrazolo[5,1-d]-[1,2,3,5]tetrazine-4(3H)-ones. In this strategy, a one-pot reaction from 5-aminopyrazoles to the pyrazolo[5,1-d]-[1,2, 3,5]tetrazine-4(3H)-ones which provided the compounds in good yields was demonstrated. Using this synthetic strategy, we prepared a representative set of 16 pyrazolo[5,1-d][l,2,3,5]tetrazine-4(3H)-ones.
Gao, Yaojun,Lam, Yulin
experimental part
p. 69 - 74
(2010/10/04)

Design, synthesis, and evaluation of 2-aryl-7-(3′,4′-dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidines as novel PDE-4 inhibitors
Described herein is design, synthesis, and biological evaluation of novel series of 2-aryl-7-(3′,4′-dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidines acting as inhibitors of type 4 phosphodiesterase (PDE4) which is known as a good target for the treatment of asthma and COPD. For this purpose, structure optimization was conducted with the aid of structure-based drug design using the known X-ray crystallography. Also, biological effects of these compounds on the target enzyme were evaluated by using in vitro assays, leading to the potent and selective PDE-4 inhibitor (IC50 10 nM).
Kim, Ikyon,Song, Jong Hwan,Park, Chang Min,Jeong, Joon Won,Kim, Hyung Rae,Ha, Jin Ryul,No, Zaesung,Hyun, Young-Lan,Cho, Young Sik,Sook Kang, Nam,Jeon, Dong Ju
scheme or table
p. 922 - 926
(2010/06/22)

Pyrazolopyrimidines and pyrazolotriazines with potent activity against herpesviruses
Synthesis of several pyrazolo[1,5-c]pyrimidines, pyrazolo[1,5-a]pyrimidines and pyrazolo[1,5-a][1,3,5]triazines with potent activity against herpes simplex viruses is described. Synthetic approaches allowing for variation of the substitution pattern are o
Gudmundsson, Kristjan S.,Johns, Brian A.,Weatherhead, Jason
scheme or table
p. 5689 - 5692
(2010/04/05)

Facile synthesis of fluorinated 2-aryl-5,7 bisalkyl pyrazolo pyrimidines from arylalkyne nitriles
Synthesis of pyrazolopyrimidines from fluorine substituted arylalkynenitriles is described. Arylalkynenitriles 1a-d reacted with hydrazine to give 5-aryl-3-amino-2H-pyrazoles 2a-d. The condensation of aminopyrazoles with 1,3-dicarbonyl compounds furnished
Rama Rao,Lingaiah,Ezikiel,Yadla,Shanthan Rao
p. 275 - 280
(2007/10/03)

Novel potent neuropeptide Y Y5 receptor antagonists: Synthesis and structure-activity relationships of phenylpiperazine derivatives
A series of phenylpiperazine derivatives were synthesized and evaluated for their neuropeptide Y (NPY) Y5 receptor antagonistic activities. The benzindane portion of 2 was replaced by 1-phenylpiperazine, resulting in novel urea derivative 3f. Subsequent optimization of the phenylpiperazine template by substitution of the phenyl moiety resulted in a series of (2-methanesulfonamidephenyl)piperazine derivatives that showed potent binding affinity and antagonistic activity for the Y5 receptor.
Takahashi, Toshiyuki,Sakuraba, Aya,Hirohashi, Tomoko,Shibata, Takunobu,Hirose, Masaaki,Haga, Yuji,Nonoshita, Katsumasa,Kanno, Tetsuya,Ito, Junko,Iwaasa, Hisashi,Kanatani, Akio,Fukami, Takehiro,Sato, Nagaaki
p. 7501 - 7511
(2007/10/03)

Microwave-assisted synthesis of N-pyrazole ureas and the p38α inhibitor BIRB 796 for study into accelerated cell ageing
Microwave irradiation of substituted hydrazines and β-ketoesters gives 5-aminopyrazoles in excellent yield, which can be transformed to the corresponding N-carbonyl derivatives by treatment with an isocyanate or chloroformate. Derivatization of 4-nitronaphth-1-ol using predominantly microwave heating methods and reaction with an N-pyrazole carbamate provides a rapid route to the N-pyrazole urea BIRB 796 in high purity, as a potent and selective inhibitor of p38α mitogen-activated protein kinase for the study of accelerated ageing in Werner syndrome cells. The Royal Society of Chemistry 2006.
Bagley, Mark C.,Davis, Terence,Dix, Matthew C.,Widdowson, Caroline S.,Kipling, David
p. 4158 - 4164
(2008/09/19)

Synthesis of β-tosylethylhydrazine and its use in preparation of N-protected pyrazoles and 5-aminopyrazoles
β-Tosylethylhydrazine (6) can be prepared efficiently in one step from commercially available p-tolyl vinyl sulfone (7) and hydrazine hydrate. This hydrazine reacts with both 1,3-diketones and conjugated ynones in glacial acetic acid to provide a variety of N-tosylethyl-protected (TSE) pyrazoles in good yields. The TSE group can be removed from the pyrazoles using potassium t-butoxide in THF at -30°C-rt. In addition, hydrazine 6 condenses with β-ketonitriles and β-aminoacrylonitriles to afford 5-aminopyrazoles, which can be deprotected by brief treatment with NaOEt in EtOH/DMSO at 45°C.
Dastrup, David M.,Yap, Amy H.,Weinreb, Steven M.,Henry, James R.,Lechleiter, Andrew J.
p. 901 - 906
(2007/10/03)

A clean and rapid synthesis of 5-amino and 5-alkoxycarbonylpyrazoles using montomorillonite under acid free conditions
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Jagath Reddy,Latha,Srinivasa Rao
p. 494 - 498
(2007/10/03)

Synthesis of some novel fluorinated pyrazolo[3,4-b]pyridines
Reaction of 5-amino-3-substituted pyrazoles (1a-c) and 5-amino-1,3- disubstituted pyrazoles (1d-i) with fluorinated-β-diketones (2) results in the formation of the single isomer of pyrazolo[3,4-b]pyridines (4a-h). A one-pot procedure for the synthesis of
Singh,Naithani, Rajesh,Aggarwal, Ranjana,Prakash, Om
p. 4359 - 4367
(2007/10/03)

Synthesis of pyrazolo[5′,1′:2,3]pyrimido[4,5-b][1,4]- benzoxazines, a new heterocyclic ring system from 5(3)-aminopyrazoles
A series of pyrazolo[5′,1′:2,3]pyrimido[4,5-b][1,4]benzoxazines (4a-n), a new heterocyclic ring system has been synthesized starting from 2H-3-oxo-[1,4]-benzoxazines (1a-d) and 5(3)-aminopyrazoles (3a-d) via the intermediates 3-chloro-2-formylidine-1,4-be
Reddy,Reddy, Pragati,Reddy, G. Jagath,Rao, K. Srinivasa
p. 163 - 166
(2007/10/03)

Substituted piperazines
Compounds are provided that act as potent antagonists of the CCR1 receptor, and which have been further confirmed in animal testing for inflammation, one of the hallmark disease states for CCR1. The compounds are generally aryl piperazine derivatives and are useful in pharmaceutical compositions, methods for the treatment of CCR1-mediated diseases, and as controls in assays for the identification of competitive CCR1 antagonists.
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(2008/06/13)

Synthesis of aminopyrazoles from α- oxoketene O,N-acetals using Montmorillonite K-10/Ultrasound
5(3)-Amino-3(5) phenylpyrazoles 3a-f have been conveniently prepared by condensation of α-oxoketene O,N-acetals 2a-g with hydrazine using montmorillonite K-10 as solid support under sonication.
Braibante, Mara E. F.,Braibante, Hugo T. S.,Da Roza, Juliano K.,Henriques, Danielle M.,De Carvalho Tavares, Luciana
p. 1160 - 1162
(2007/10/03)

1-ARYL-4-SUBSTITUTED PIPERAZINES DERIVATIVES FOR USE AS CCR1 ANTAGONISTS FOR THE TREATMENT OF INFLAMMATION AND IMMUNE DISORDERS
Compounds are provided that act as potent antagonists of the CCR1 receptor, and which have been further confirmed in animal testing for inflammation, one of the hallmark disease states for CCR1. The compounds are generally aryl piperazine derivatives and are useful in pharmaceutical compositions, methods for the treatment of CCR1-mediated diseases, and as controls in assays for the identification of competitive CCR1 antagonists.
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Page 62

(2008/06/13)

Synthesis of N-alkylated derivatives of pyrazolo[1,5-a]-pyrimidine and their reaction with methylamine
With the object of studying the factors influencing the course of enamine rearrangements, we have carried out the N-alkylation of alkyl- and aryl-substituted pyrazolo[1,5-a]pyrimidines. Using the NOEDIF NMR spectroscopic method for the cases of 5,7-dimeth
Danagulyan,Panosyan,Boyakhchyan
p. 581 - 585
(2007/10/03)

Pyrazolopyrimidines based on 5-aminopyrazoles unsubstituted at the position 1
By condensation of various symmetric β-diketones with a series of 5-aminopyrazoles that are unsubstituted at the position 1, we have obtained a series of pyrazolo[1,5-a]pyrimidines that are of interest as physiologically active compounds. Hexafluoroacetylacetone reacts in another direction, forming pyrazolo[4,5-b]pyridine.
Nam,Grandberg,Sorokin
p. 1371 - 1374
(2007/10/03)

The Preparation of N-(1H-Pyrazol-3-yl)arylamides and 1H-Pyrazol-3-amines from Polylithiated C(α)N-Thiosemicarbazones and C(α),N-Semicarbazones
C(α),N-Tbiosemlcarbazones or C(α),N-semicarbazones were polylithiated with excess lithium diisopropylamide, and the resulting cyclized intermediates were condensed with aromatic esters to afford N-(1H-pyrazol-3-yl)arylamides. The polylithiated intermediates were also quenched with aqueous acid to give 5-substituted, 1H-pyrazol-3-amines.
Beam, Charles F.,Davis, Sharon E.,Cordray, Tracy L.,Chan, Kam W.,Kassis, Camille M.,Freeman Davis, Joanna G.,Mark Latham,Guion, Tina S.,Hildebran, Karen C.,Church, A. Cameron,Koller, Madlene U.,Metz, Clyde R.,Pennington, William T.,Schey, Kevin L.
p. 1549 - 1554
(2007/10/03)

NITROAZINES. 15. CONTRACTION OF THE PYRIMIDINE RING IN 6-NITROAZOLOPYRIMIDINES
It is shown that contraction of the pyrimidine ring occurs when 6-nitro-7-oxo-4,7-dihydroazolopyrimidines are heated with hydrazine hydrate.Complexes of 4-nitropyrazole with 5-aminoazoles, the structures of which were proved by x-ray diffraction analysis, are formed in a similar reaction of nitrosubstituted azolopyrimidines that do not contain an oxo function.
Rusinov, V. L.,Myasnikov, A. V.,Chupakhin, O. N.,Aleksandrov, G. G.
p. 530 - 533
(2007/10/02)

A Facile Synthesis of 5-Aminopyrazoles by the Reaction of β-Chlorocinnamonitriles with Hydrazine Hydrate
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Hartmann, Horst,Liebscher, Juergen
p. 276 - 277
(2007/10/02)

Allenes. Part 39. The Synthesis of 3-Alkyl-5-aminopyrazoles and 3H-Indoles from Allenic or Acetylenic Nitriles
Hydrazine adds to allenic or acetylenic nitriles to give 3-alkyl-substituted 5-aminopyrazoles in excellent yields.Conjugated and unconjugated enaminic nitriles may be isolated from the Michael addition of phenylhydrazine to allenic nitriles and ring-close
Fomum, Z. Tanee,Landor, Stephen R.,Landor, Phyllis D.,Mpango, George W. P.
p. 2997 - 3001
(2007/10/02)