Hydroxy Derivatives of Poststerone and Its Nontrivial 13(14→8)-Abeo-analogues: Synthesis, Crystal Packing, and Intermolecular Hydrogen Bonds

Савченко, Р. Г.; Mescheryakova, Ekaterina S.; Bikmukhametov, Kamil Sh.; Tulyabaev, Arthur R.; Parfenova, Lyudmila V.

doi:10.1016/j.molstruc.2020.129509

Cited by 5 publications

(7 citation statements)

References 56 publications

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“…This is in accordance with the literature reports of secondary amides. 53,54 As a result, NMR analysis ( 1 H, 13 C and 15 N) confirmed that the reaction product is compound C and is consistent with the literature. 55,56 Biology Carbonic anhydrase inhibition and structure-activity relationship (SAR).…”

Section: Chemistrysupporting

confidence: 89%

“…Three mechanisms can be suggested on the basis of our synthetic route, and are shown in Scheme 2 and explained in detail. Compound A was excluded because the CQS bond has been consistently reported in the literature 50 at around d 183 ppm, and there was no signal in this region in our 13 C NMR analysis. In the 1 H NMR spectrum, an N-H proton appeared at d 12.42 ppm, which is consistent with a lactam proton.…”

Section: Chemistrymentioning

confidence: 97%

“…Finally, these electrophiles (5a-5j) and the potassium thiocyanate were combined with dry ethanol and refluxed for 10-12 hours to form targeted compounds 2-((5-phenyl/benzyl-1,3,4-thiadiazol-2-yl)imino)thiazolidin-4-ones (7a-7j) in reasonable yields. Different analytical techniques, including FT-IR, 1 H NMR, 13 C NMR, 2D-NMR (COSY, HSQC, and HMBC) and 15 N NMR, were applied to characterize the final synthetic compounds.…”

Section: Chemistrymentioning

confidence: 99%

“…[3][4][5][6][7][8][9] Carbonic anhydrases play a crucial role in a number of physiological processes. Therefore, abnormal CA levels and/or activities have been reported to be related to a variety of human diseases such as Alzheimer's disease, 10 epilepsy, 11 stroke, 12 obesity, 13 edema, 14 altitude sickness, 15 and several types of cancer. 16 As a result, CA isozymes motivate and encourage scientists, particularly medicinal chemists, to research the development of new CA inhibitors.…”

mentioning

confidence: 99%

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Design, synthesis, and in vitro and in silico studies of 1,3,4-thiadiazole-thiazolidinone hybrids as carbonic anhydrase inhibitors

et al. 2023

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Section: Chemistrysupporting

confidence: 89%

Section: Chemistrymentioning

confidence: 97%

Section: Chemistrymentioning

confidence: 99%

mentioning

confidence: 99%

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Design, synthesis, and in vitro and in silico studies of 1,3,4-thiadiazole-thiazolidinone hybrids as carbonic anhydrase inhibitors

et al. 2023

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“…Reaction of abeo -pregnanes with complex metal hydrides has been reported for 6- and 20-oxo-groups; however, the 14-oxo-group reactivity was decreased. In 6,20-dioxo-Δ2,3-pregnane and 6,20,14-trioxo-13(14 → 8)- abeo -isomer structures, the reduction of hydride is stereospecific, giving 6α,20 R -diols [ 137 ].…”

Section: Structure Of Phytoecdysteroidsmentioning

confidence: 99%

Phytoecdysteroids: Distribution, Structural Diversity, Biosynthesis, Activity, and Crosstalk with Phytohormones

Arif

Singh

Bajguz

et al. 2022

IJMS

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Phytoecdysteroids (PEs) are naturally occurring polyhydroxylated compounds with a structure similar to that of insect molting hormone and the plant hormone brassinosteroids. PEs have a four-ringed skeleton composed of 27, 28, 29, or 30 carbon atoms (derived from plant sterols). The carbon skeleton of ecdysteroid is known as cyclopentanoperhydrophenanthrene and has a β-sidechain on C-17. Plants produce PEs via the mevalonate pathway with the help of the precursor acetyl-CoA. PEs are found in algae, fungi, ferns, gymnosperms, and angiosperms; more than 500 different PEs are found in over 100 terrestrial plants. 20-hydroxyecdysone is the most common PE. PEs exhibit versatile biological roles in plants, invertebrates, and mammals. These compounds contribute to mitigating biotic and abiotic stresses. In plants, PEs play a potent role in enhancing tolerance against insects and nematodes via their allelochemical activity, which increases plant biological and metabolic responses. PEs promote enzymatic and non-enzymatic antioxidant defense systems, which decrease reactive oxygen species in the form of superoxide radicals and hydroxyl radicals and reduce malondialdehyde content. PEs also induce protein biosynthesis and modulate carbohydrate and lipid synthesis. In humans, PEs display biological, pharmacological, and medicinal properties, such as anti-diabetic, antioxidant, anti-microbial, hepatoprotective, hypoglycemic, anti-cancer, anti-inflammatory, antidepressant, and tissue differentiation activity.

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Ecdysteroids: isolation, chemical transformations, and biological activity

et al. 2022

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Hydroxy Derivatives of Poststerone and Its Nontrivial 13(14→8)-Abeo-analogues: Synthesis, Crystal Packing, and Intermolecular Hydrogen Bonds

Cited by 5 publications

References 56 publications

Design, synthesis, and in vitro and in silico studies of 1,3,4-thiadiazole-thiazolidinone hybrids as carbonic anhydrase inhibitors

Design, synthesis, and in vitro and in silico studies of 1,3,4-thiadiazole-thiazolidinone hybrids as carbonic anhydrase inhibitors

Phytoecdysteroids: Distribution, Structural Diversity, Biosynthesis, Activity, and Crosstalk with Phytohormones

Ecdysteroids: isolation, chemical transformations, and biological activity

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