78583-81-0

Usage

Synthesis Reference(s)

Synthesis, p. 276, 1984 DOI: 10.1055/s-1984-30809

InChI:InChI=1/C9H8ClN3/c10-7-3-1-6(2-4-7)8-5-9(11)13-12-8/h1-5H,(H3,11,12,13)

Upstream product

• 78583-86-5 (E)-3-Chloro-3-(4-chloro-phenyl)-acrylonitrile 
• 150059-52-2 (E)-1-[1-(4-chlorophenyl)ethylidene]thiosemicarbazide 
• 4640-66-8 p-chlorobenzoylacetonitrile 
• 90272-22-3 2-chloro-3-(4-chlorophenyl)acrylonitrile 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 138175-62-9 (E)-3-Bromo-3-(4-chloro-phenyl)-2-ethylsulfanyl-acrylonitrile 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 74-11-3 para-chlorobenzoic acid 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 375360-09-1 2-(4-chlorophenyl)-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidine 

Relevant academic research and scientific papers

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.

Modular synthesis and antiproliferative activity of new dihydro-1H-pyrazolo[1,3-b]pyridine embelin derivatives

A set of new dihydro-1H-pyrazolo[1,3-b]pyridine and pyrazolo[1,3-b]pyridine embelin derivatives was synthesized through a multicomponent reaction from natural embelin, 3-substituted-5-aminopyrazoles and aldehydes. The synthesized compounds were evaluated against three hematologic tumor cell lines, HEL (acute erythroid leukemia), K-562 (chronic myeloid leukemia) and HL-60 (acute myeloid leukemia), and five breast cancer cell lines (SKBR3, MCF-7, MDA-MB-231, BT-549, HS-578T). The primate non-malignant kidney Vero cell line was used as the control of cytotoxicity. From the obtained results, some structure–activity relationships were out-lined. Furthermore, in silico prediction of physicochemical properties and ADME parameters were determined for the derivatives with the best antiproliferative values.

PHARMACOLOGICALLY ACTIVE ARYL-SUBSTITUTED PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVES

The present invention relates to new pyrazolo[1,5-a]pyrimidine derivatives of formula (I) or pharmaceutically acceptable salts, biologically active metabolites, pro-drugs, racemates, enantiomers, diastereomers, solvates and hydrates thereof that serve as GABAB receptor positive allosteric modulators. The invention also relates to the process for producing such compounds. The invention further relates to pharmaceutical compositions comprising such compounds optionally in combination with two or more different therapeutic agents and the use of such compounds in methods for treating diseases and conditions mediated and modulated by the GABAB receptor positive allosteric mechanism. The invention also provides a method for manufacture of medicaments useful in the treatment of such disorders.

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.

"On-Water" Facile Synthesis of Novel Pyrazolo[3,4-b]pyridinones Possessing Anti-influenza Virus Activity

A facile and versatile "on-water" protocol for the synthesis of pyrazolo[3,4-b]pyridinones was developed by the unprecedented construction of two rings and five new bonds in one-pot. It was proved that water was an important promoter of the reaction and P

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.

BENZENE SULFONAMIDES AS CCR9 INHIBITORS

The present invention relates to compounds useful as CCR9 modulators, to compositions containing them, to methods of making them, and to methods of using them. In particular, the present invention relates to compounds capable of modulating the function of the CCR9 receptor by acting as partial agonists, antagonists or inverse agonists. Such compounds may be useful to treat, prevent or ameliorate a disease or condition associated with CCR9 activation, including inflammatory and immune disorder diseases or conditions such as inflammatory bowel diseases (IBD).

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

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 -

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).