Novel synthesis and reactions of pyrazolyl-substituted tetrahydrothieno[2,3-<i>c</i>]isoquinoline derivatives

Zaki, Remon M.; Dean, Adel M. Kamal El; Monem, Maisa I. Abd El; Seddik, Mohamed A.

doi:10.1515/hc-2015-0204

Cited by 10 publications

(4 citation statements)

References 17 publications

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“…Finally, N -(arylidineamino)pyrrolopyrimidine-4-amines 8(a–f) were obtained from the condensation reaction of 2(a–b) with different aromatic aldehydes. The structures of all the produced compounds were supported with elemental analysis and spectral data 51 , 53 .…”

Section: Resultsmentioning

confidence: 94%

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Novel pyrrolopyrimidine derivatives: design, synthesis, molecular docking, molecular simulations and biological evaluations as antioxidant and anti-inflammatory agents

Sayed

Mansour

Ali

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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Current medical approaches to control the Covid-19 pandemic are either to directly target the SARS-CoV-2 via innovate a defined drug and a safe vaccine or indirectly target the medical complications of the virus. One of the indirect strategies for fighting this virus has been mainly dependent on using anti‐inflammatory drugs to control cytokines storm responsible for severe health complications. We revealed the discovery of novel fused pyrrolopyrimidine derivatives as promising antioxidant and anti-inflammatory agents. The newly synthesised compounds were evaluated for their in vitro anti-inflammatory activity using RAW264.7 cells after stimulation with lipopolysaccharides (LPS). The results revealed that 3a, 4b, and 8e were the most potent analogues. Molecular docking and simulations of these compounds against COX-2, TLR-2 and TLR-4 respectively was performed. The former results were in line with the biological data and proved that 3a, 4b and 8e have potential antioxidant and anti-inflammatory effects.

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Section: Resultsmentioning

confidence: 94%

“…The remarkable biological activity of pyrrolopyrimidines and fused pyrrolopyrimidine derivatives 51–54 has inspired us to synthesise new derivatives and test their anti-inflammatory activity 55 , 56 . The synthetic strategies for our target compounds are presented in Scheme 1 .…”

Section: Resultsmentioning

confidence: 99%

Novel pyrrolopyrimidine derivatives: design, synthesis, molecular docking, molecular simulations and biological evaluations as antioxidant and anti-inflammatory agents

Sayed

Mansour

Ali

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In the light of the prior biological activities of tetrahydroisoquinolines and in resumption of our project for synthesis of new heterocycles containing the thienotetrahydroisoquinolines moiety, − we have announced here preparation of the new 1-amino-2-substituted and 1-pyrrolyl-2-substituted-5-piperidinyl-6,7,8,9-tetrahydrothieno[2,3- c ]isoquinolines and their fused heterocycles which have proved promising antibacterial and antifungal activities parallel to the standard drugs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Novel Piperidinyl Tetrahydrothieno[2,3-c]isoquinolines and Related Heterocycles

et al. 2019

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A novel series of 1-amino-2-substituted-5- piperidinyl-6,7,8,9-tertahydrothieno[2,3-c]isoquinolines (4a−e) was synthesized upon treatment of 4-cyano-1-piperidinyl-5,6,7,8-tetrahydroisoquinline-3(2H)-thione (2) with α-halo carbonyl compounds such as chloroacetone, ethyl chloroacetate, 2-bromoacetophenone, chloroacetamide, and chloroacetanilide. Construction the pyrrolyl ring associated with the thienotetrahydroisoquinoline moiety was achieved by treatment of compounds 4a, b with 2,5-dimethoxytertahydrofuran in acetic acid. 1-Pyrrolyl-2-substituted-thieno[2,3-c]isoquinolines 5a and 5b which in turn were used as multipurpose precursors for synthesis of other new heterocycles. Assignments of the chemical structures of the respectively synthesized thienotetrahydroisoquinolines and their derivatives were established on the bases of elemental and spectral techniques (Fourier transform infrared, 1 H NMR, 13 C NMR, and mass spectroscopy). Furthermore, certain compounds were screened for their antimicrobial activity which revealed promising activities against various pathogenic strains of bacteria and fungi.

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“…Recently, a large number of thienopyrimidines and fused thienopyrimidines were found to possess promising anti‐inflammatory and antimicrobial activities, as shown in Figure . Based on the above‐mentioned facts, and in continuation of our work on biologically active nitrogen and sulfur heterocycles, we report here the synthesis of some new thienopyrimidine derivatives aiming at developing more active antimicrobial and anti‐inflammatory agents.…”

Section: Introductionmentioning

confidence: 95%

Synthesis, reactions, and biological study of some new thienopyrimidine derivatives as antimicrobial and anti‐inflammatory agents

Tolba¹,

El‐Dean

Ahmed³

et al. 2018

J Chinese Chemical Soc

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Pyrimidine and thienopyrimidine derivatives play a very important role in organic chemistry because of their wide applications as bioactive compounds with multiple biological activities. However, a literature survey revealed that the merger of different groups in the thieno[2,3-d]pyrimidine heterocyclic ring enhances its antibacterial, antifungal and anti-inflammatory activities. This encouraged us to prepare a new series of thieno[2,3-d]pyrimidine heterocyclic compounds and to test them as antimicrobial and anti-inflammatory agents. These compounds have shown remarkable activity toward fungi, bacteria, and inflammation. Thus, these compounds have been prepared by the chloroacylation of 5-amino-4-phenyl-2-(p-tolylamino) thieno[2,3-d] pyrimidine-6-carboxamide (4) using chloroacetyl chloride under neat condition to afford the target compound (6), which was used as precursor for the synthesis of a number of bioactive compounds. Thus reaction of the chloromethylpyrimidine derivative (6) with triphenylphosphine in dry benzene gave the corresponding ((4-oxo-9-phenyl-7-(p-tolylamino)-3,4-dihydropyrimido[4 0 ,5 0 :4,5]thieno [2,3-d]pyrimidin-2-yl)methyl) triphenylphosphonium chloride (7). Compounds 8a-8c and 9a-9c were obtained by the reaction of 7 with some selected aromatic aldehydes and ketones in methanol and sodium methoxide under Wittig reaction condition. The structures of the all new synthesized compounds were established on the basis of their analytical and spectral data (IR, 1 H NMR, 13 C NMR, and MS).

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Novel synthesis and reactions of pyrazolyl-substituted tetrahydrothieno[2,3-c]isoquinoline derivatives

Cited by 10 publications

References 17 publications

Novel pyrrolopyrimidine derivatives: design, synthesis, molecular docking, molecular simulations and biological evaluations as antioxidant and anti-inflammatory agents

Novel pyrrolopyrimidine derivatives: design, synthesis, molecular docking, molecular simulations and biological evaluations as antioxidant and anti-inflammatory agents

Synthesis and Antimicrobial Activity of Novel Piperidinyl Tetrahydrothieno[2,3-c]isoquinolines and Related Heterocycles

Synthesis, reactions, and biological study of some new thienopyrimidine derivatives as antimicrobial and anti‐inflammatory agents

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