3,5-Dialkyl-4-hydroxybenzylidenemalononitrile; A New Group of Fungicidal and Acaricidal Agents

Horiuchi, Fukashi; Fujimoto, Keimei; Ozaki, Tatsuo; Nishizawa, Yoshihiko

doi:10.1080/00021369.1971.10860197

Cited by 2 publications

(5 citation statements)

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“…Workup gave 0.2 g of yellow-green solid: 29% yield; mp 260 °C; NMR (acetone-d6) 6. 24 (1 H, t, J = 2.0 Hz, H4), 6.74 (2 H, d, J = 2.0 Hz, H26), 7.70 (1 H, s, vinylic proton). Anal.…”

Section: Methodsmentioning

confidence: 99%

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Tyrphostins I: synthesis and biological activity of protein tyrosine kinase inhibitors

Gazit¹,

Yaish²,

Gilon³

et al. 1989

J. Med. Chem.

584

346

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A novel class of low molecular weight protein tyrosine kinase inhibitors is described. These compounds constitute a systematic series of molecules with a progressive increase in affinity toward the substrate site of the EGF receptor kinase domain. These competitive inhibitors also effectively block the EGF-dependent autophosphorylation of the receptor. The potent EGF receptor kinase blockers examined were found to competitively inhibit the homologous insulin receptor kinase at 10(2)-10(3) higher inhibitor concentrations in spite of the significant homology between these protein tyrosine kinases. These results demonstrate the ability to synthesize selective tyrosine kinase inhibitors. The most potent EGF receptor kinase inhibitors also inhibit the EGF-dependent proliferation of A431/clone 15 cells with little or no effect on EGF independent cell growth. These results demonstrate the potential use of protein tyrosine kinase inhibitors as selective antiproliferative agents for proliferative diseases caused by the hyperactivity of protein tyrosine kinases. We have suggested the name "tyrphostins" for this class of antiproliferative compounds which act as protein tyrosine kinase blockers.

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“…Workup gave 0.2 g of yellow-green solid: 29% yield; mp 260 °C; NMR (acetone-d6) 6. 24 (1 H, t, J = 2.0 Hz, H4), 6.74 (2 H, d, J = 2.0 Hz, H26), 7.70 (1 H, s, vinylic proton). Anal.…”

Section: Methodsmentioning

confidence: 99%

“…Anal. (3,4-Dihydroxy-5-methoxybenzylidene)malononitrile (24) (Method D). To 0.46 g (2 mM) of 4 in 30 mL of trichloroethylene were added 0.3 g (1.1 mM) of A1C13 and 0.8 mL of pyridine.…”

Section: Methodsmentioning

confidence: 99%

Tyrphostins I: synthesis and biological activity of protein tyrosine kinase inhibitors

Gazit¹,

Yaish²,

Gilon³

et al. 1989

J. Med. Chem.

584

346

View full text Add to dashboard Cite

show abstract

“…All final products were isolated and purified. All products were deduced from their FT-IR, 1 H NMR, and 13 C NMR spectral data along with elemental analyses (C, H, N), and their melting point.…”

Section: Methodsmentioning

confidence: 99%

“…[6][7][8][9] The profound biological potential of α,β-unsaturated compounds has cast them as captivating molecules, beckoning the interest of chemists and pharmacologists. These compounds have showcased an extensive and diverse spectrum of biological activities, spanning anti-nociception through TREK-1 channel modulation, [10,11] inhibition of 12-Lipoxygenase, [12] acaricidal-fungicidal attributes, [13] antagonism of NMDA receptors, [14] and therapeutic potential for circulatory system diseases. [15] They have even ventured into the realm of antitumor activity.…”

Section: Introductionmentioning

confidence: 99%

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Unraveling the Anticancer Potential of Cinnamonitrile Derivatives: In vitro Evaluation and Molecular Docking

Faghih‐Mirzaei,

Kavousi,

Langarizadeh

et al. 2023

ChemistrySelect

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Cancer remains a formidable global healthcare challenge, driving relentless research efforts. Among the diverse compounds explored for their potential in combating cancer, α,β‐unsaturated compounds have exhibited intriguing biological activities, including anticancer properties. In this study, we embarked on synthesizing novel α,β‐unsaturated compounds anchored by a phenylacrylonitrile base using the Knoevenagel reaction. Our investigation delved into the cytotoxicity of these compounds, where two standouts, 3 f and 3 g, demonstrated remarkable antiproliferative efficacy comparable to the established chemotherapy drug, doxorubicin, when tested against various cancer cell lines. Additionally, the influence of these compounds was evident as DNA fragmentation became apparent after a mere 24‐hour exposure. Molecular docking analysis unveiled a compelling interaction between our synthesized compounds and the P38‐α receptor, a pivotal player in the Mitogen‐Activated Protein (MAP) kinase 14 pathway. This revelation suggests the potential of our compounds to target this receptor, opening new avenues for further exploration. Our research not only underscores the promising anticancer potential of these α,β‐unsaturated compounds but also identifies a specific molecular target, P38‐α, paving the way for future investigations in cancer therapeutics. In an ever‐evolving quest to combat cancer, this study contributes valuable insights that may hold the key to innovative treatment strategies.

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3,5-Dialkyl-4-hydroxybenzylidenemalononitrile; A New Group of Fungicidal and Acaricidal Agents

Cited by 2 publications

References 0 publications

Tyrphostins I: synthesis and biological activity of protein tyrosine kinase inhibitors

Tyrphostins I: synthesis and biological activity of protein tyrosine kinase inhibitors

Unraveling the Anticancer Potential of Cinnamonitrile Derivatives: In vitro Evaluation and Molecular Docking

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