827-41-8

Usage

Chemical Properties

Pale Yellow Solid

Upstream product

• 2492-30-0 acetophenone semicarbazone 
• 60-29-7 diethyl ether 
• 693-04-9 butyl magnesium bromide 
• 78583-84-3 (Z)-3-chloro-3-phenyl-2-propenenitrile 
• 17539-55-8 acetophenone-(E)-semicarbazone 
• 74-89-5 methylamine 
• 614-16-4 Benzoylacetonitrile 
• 91132-63-7 (E)-3-Amino-3-ethoxy-1-phenyl-2-propen-1-on 
• 16516-19-1 O-ethyl 3-oxo-3-phenylpropanethioate 
• 7391-28-8 p-tolueneacetonitrile 
• 80-17-1 benzenesufonyl hydrazide 
• 93-89-0 benzoic acid ethyl ester 
• 70-11-1 α-bromoacetophenone 
• 138175-61-8 β-bromo-α-(ethylsulfanyl)cinnamonitrile 

Downstream Products

• 28648-96-6 2-phenyl-4H-pyrazolo[1,5-a]pyrimidine-5,7-dione 
• 60419-87-6 4,5-diphenyl-1,6⁽⁷⁾-dihydro-pyrazolo[3,4-c][1,2]thiazine 2,2-dioxide 
• 89819-57-8 7-hydroxy-2-phenyl-5-(γ-pyridyl)-pyrazolo<1,5-a>pyrimidine 
• 50671-40-4 N-(3-phenyl-1H-pyrazol-5-yl)acetamide 
• 65774-92-7 5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 136773-52-9 5-Methyl-2-phenylpyrazolo<5,1-a>quinazoline 
• 87379-22-4 5-Oxo-2,7-diphenyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidine-6-carbonitrile 
• 133549-57-2 6-Methyl-2-phenyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidine-5,8-dione 
• 122164-26-5 7-(4-Nitro-phenyl)-2,5-diphenyl-pyrazolo[1,5-a]pyrimidine 
• 129095-32-5 6-cyclohexyl-4,7-dihydro-2-phenyl-5H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidine-5,8(6H)-dione 
• 95650-19-4 5,7-Diamino-2-phenyl-pyrazolo<1,5-a>pyrimidin 
• 122164-23-2 2,5,7-triphenylpyrazolo<1,5-a>pyrimidine 
• 122164-14-1 2,5,7-triphenyl-6,7-dihydropyrazolo<1,5-a>pyrimidine 
• 105949-97-1 2,3-Dimethyl-7-phenylpyrazole<1,5-b><1,2,4>triazine 

Relevant academic research and scientific papers

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

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.

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).

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.

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).

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.

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.

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

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.

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