Synthesis and Biological Evaluation of N-Cinnamoyl and Mandelate Metformin Analogues

Kumari, Vandana; Bharathi, K.; Prabhu, Kandikere Ramaiah; Ponnudurai, K

doi:10.14233/ajchem.2016.19633

Cited by 3 publications

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“…All starting compounds were purchased from the usual providers and used without further purification. Substituted cinnamic acids 2 a – c and 5 a – d were prepared as reported previously [37,38] . Column chromatography: silica gel 60 (230–400 mesh).…”

Section: Methodsmentioning

confidence: 99%

“…Substituted cinnamic acids 2 a-c and 5 a-d were prepared as reported previously. [37,38] Column chromatography: silica gel 60 (230-400 mesh). Melting points (uncorrected), Electrothermal 9100; NMR spectra, Bruker Avance 300 spectrometer; chemical shifts are given in parts per million (δ) downfield from tetramethylsilane as internal standard; Mass spectra, Thermo Finnigan MAT 8500 (EI).…”

Section: Experimental Section Generalmentioning

confidence: 99%

“…Yield: 70 mg (0.22 mmol, 54 %); offwhite solid of m.p. 107-109 °C; R f = 0.59 (ethyl acetate/n-hexane, 1 : 1); υ max (ATR)/cm ), 141.5 (olefin-C), 146.9 (ArÀ C q ), 153.8 (ArÀ C q ), 169.3 (CO), 173.9 (CO); m/z (%) 325 (37)…”

Section: (E)-1-[3-(3-chloro-45-dimethoxyphenyl)acryloyl]piperidin-2-o...mentioning

confidence: 99%

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Evaluation of the Antiparasitic and Antifungal Activities of Synthetic Piperlongumine‐Type Cinnamide Derivatives: Booster Effect by Halogen Substituents

et al. 2023

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A series of synthetic N‐acylpyrrolidone and ‐piperidone derivatives of the natural alkaloid piperlongumine were prepared and tested for their activities against Leishmania major and Toxoplasma gondii parasites. Replacement of one of the aryl meta‐methoxy groups by halogens such as chlorine, bromine and iodine led to distinctly increased antiparasitic activities. For instance, the new bromo‐ and iodo‐substituted compounds 3 b/c and 4 b/c showed strong activity against L. major promastigotes (IC50=4.5–5.8 μM). Their activities against L. major amastigotes were moderate. In addition, the new compounds 3 b, 3 c, and 4 a–c exhibited high activity against T. gondii parasites (IC50=2.0–3.5 μM) with considerable selectivities when taking their effects on non‐malignant Vero cells into account. Notable antitrypanosomal activity against Trypanosoma brucei was also found for 4 b. Antifungal activity against Madurella mycetomatis was observed for compound 4 c at higher doses. Quantitative structure‐activity relationship (QSAR) studies were carried out, and docking calculations of test compounds bound to tubulin revealed binding differences between the 2‐pyrrolidone and 2‐piperidone derivatives. Microtubules‐destabilizing effects were observed for 4 b in T. b. brucei cells.

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Section: Methodsmentioning

confidence: 99%

Section: Experimental Section Generalmentioning

confidence: 99%

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Evaluation of the Antiparasitic and Antifungal Activities of Synthetic Piperlongumine‐Type Cinnamide Derivatives: Booster Effect by Halogen Substituents

et al. 2023

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Alkylacylimidazoles in Claisen–Schmidt and Knoevenagel Condensations

Quan

Wang

et al. 2020

Russ J Org Chem

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Targeting AMPK in Diabetes and Diabetic Complications: Energy Homeostasis, Autophagy and Mitochondrial Health

Madhavi

Gaikwad

Yerra

et al. 2019

CMC

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Adenosine 5'-monophosphate activated protein kinase (AMPK) is a key enzymatic protein involved in linking the energy sensing to the metabolic manipulation. It is a serine/threonine kinase activated by several upstream kinases. AMPK is a heterotrimeric protein complex regulated by AMP, ADP, and ATP allosterically. AMPK is ubiquitously expressed in various tissues of the living system such as heart, kidney, liver, brain and skeletal muscles. Thus malfunctioning of AMPK is expected to harbor several human pathologies especially diseases associated with metabolic and mitochondrial dysfunction. AMPK activators including synthetic derivatives and several natural products that have been found to show therapeutic relief in several animal models of disease. AMP, 5-Aminoimidazole-4-carboxamide riboside (AICA riboside) and A769662 are important activators of AMPK which have potential therapeutic importance in diabetes and diabetic complications. AMPK modulation has shown beneficial effects against diabetes, cardiovascular complications and diabetic neuropathy. The major impact of AMPK modulation ensures healthy functioning of mitochondria and energy homeostasis in addition to maintaining a strict check on inflammatory processes, autophagy and apoptosis. Structural studies on AMP and AICAR suggest that the free amino group is imperative for AMPK stimulation. A769662, a non-nucleoside thienopyridone compound which resulted from the lead optimization studies on A-592107 and several other related compounds are reported to exhibit promising effect on diabetes and its complications through activation of AMPK. Subsequent to the discovery of A769662, several thienopyridones, hydroxybiphenyls pyrrolopyridones have been reported as AMPK modulators. The review will explore the structure function relationships of these analogues and the prospect of targeting AMPK in diabetes and diabetic complications.

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Synthesis and Biological Evaluation of N-Cinnamoyl and Mandelate Metformin Analogues

Cited by 3 publications

References 0 publications

Evaluation of the Antiparasitic and Antifungal Activities of Synthetic Piperlongumine‐Type Cinnamide Derivatives: Booster Effect by Halogen Substituents

Evaluation of the Antiparasitic and Antifungal Activities of Synthetic Piperlongumine‐Type Cinnamide Derivatives: Booster Effect by Halogen Substituents

Alkylacylimidazoles in Claisen–Schmidt and Knoevenagel Condensations

Targeting AMPK in Diabetes and Diabetic Complications: Energy Homeostasis, Autophagy and Mitochondrial Health

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