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Secondary Metabolites from Clerodendrum Infortunatum L.: Their Bioactivities and Health Benefits
Published in Hafiz Ansar Rasul Suleria, Megh R. Goyal, Health Benefits of Secondary Phytocompounds from Plant and Marine Sources, 2021
R. L. Helen, K. Jayesh, S. Syama, M. S. Latha
Phenylpropanoids are the most diverse group of organic compounds, which include simple low molecular weight phenolic acids, coumarins, and benzoic acid derivatives to complex flavonoids, stilbenes, tannins, and lignans [45]. They are obtained from six carbon phenyl group and the three-carbon propene tail of cinnamic acid, produced during the initial step in the phenylpropanoid pathway [89]. They provide protection against biotic and abiotic stresses, UV radiation, herbivore, and pathogen attack and serve as signaling molecules to mediate bio-interactions [83].
Methsuximide
Published in Stanley R. Resor, Henn Kutt, The Medical Treatment of Epilepsy, 2020
Phenyl group substitution at the 2C position counteracts experimentally induced maximal electroshock seizures (MES), whereas alkyl group substitution at the 2C position counteracts experimentally induced pentylenetetrazol (PTZ) seizures. Methyl group substitution at the 5N position adds to the anti-PTZ effect and the sedative activity of the molecule. Alkyl substitution at the 5N and 2C positions and phenyl substitution at the 2C position provide both anti-PTZ-and anti-MES-induced seizure activity (1). The majority of commonly used antiepileptic drugs (AEDs) effective against complex partial seizures (CPSs) [e.g., phenytoin (PHT), phenobarbital (PB), primidone (PRM)], have a heterocyclic ring with one or more phenyl ring substituents (2).
Dietary Isoflavones-Mechanism and Efficacy in Cancer Prevention and Treatment
Published in Sheeba Varghese Gupta, Yashwant V. Pathak, Advances in Nutraceutical Applications in Cancer, 2019
Richa Dayaramani, Jayvadan K. Patel
Chemically, they are heterocyclic compounds having a chemical name as 3-phenyl-4H-chrome-4-one or 4H-1-benzopyran-4-one. They differ from flavones in the location of the phenyl group, which is found attached to the second carbon in the latter. Their molecular formula is C15H10O2 and molecular weight is 222.243 g/mol. The basic structure of isoflavone is shown in Figure 15.3.
Synthesis and biological activity evaluation of 3-(hetero) arylideneindolin-2-ones as potential c-Src inhibitors
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2022
Salvatore Princiotto, Loana Musso, Fabrizio Manetti, Valentina Marcellini, Giovanni Maga, Emmanuele Crespan, Cecilia Perini, Nadia Zaffaroni, Giovanni Luca Beretta, Sabrina Dallavalle
The percentage of inhibition at the concentrations of 100 μM and 10 μM, ID50 of the most active compounds, and their Ki were evaluated and reported in Table 3. Compounds 32–34 showed a good inhibitory activity towards the enzyme, with 34 having the best profile of inhibition (85% at 10 µM). Conversely, 36, with a carboxylic group directly linked to the phenyl ring, had very low activity. However, the percentage of inhibition was enhanced by increasing the length of the spacer between the aromatic ring and the acidic group (46, 70% at 100 µM, 47 94% at 100 µM), with the corresponding esters (43 and 44) showing a good activity as well. Replacement of the acidic group of 46 with a hydrophobic cyclopropyl substituent led to an almost inactive compound (45). Moreover, the phenolic derivative 35 and the corresponding benzyl ether 37 maintained high inhibitory activity at the highest dose, which significantly decreased at 10 µM. The shift of a lipophilic aromatic ring to meta position on the phenyl group (38) did not influence the activity. Among compounds containing heterocyclic rings, 50 showed the best activity at both concentrations, whereas the thiophene- and thiazole-containing compounds 48 and 49, respectively, evidenced a drop in activity, in particular at the lowest concentration.
Synthesis and biological evaluation of thieno[3,2-c]pyrazol-3-amine derivatives as potent glycogen synthase kinase 3β inhibitors for Alzheimer’s disease
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2022
Ning Yan, Xiao-Long Shi, Long-Qian Tang, De-Feng Wang, Xun Li, Chao Liu, Zhao-Peng Liu
At first, the effects of the acyl or sulphonyl groups at the thieno[3,2-c]pyrazol-3-amine on GSK-3β inhibitory activities were investigated. As shown in Scheme 1 and Table 1, the cyclopropanecarbonyl and the isobytyryl group showed similar effects on the GSK-3β inhibitory potency. Compounds 16a and 16b were very potent GSK-3β inhibitors with the IC50 values of 4.4 nM and 3.1 nM, respectively. When the thieno[3,2-c]pyrazol-3-amine was substituted by the n-butyryl (16c) or benzoyl (16e), the resulting compound 16c or benzoyl 16e maintained high potency, but was about 10-fold less active than 16b. However, the sulphonamide 16d showed very weak GSK-3β inhibitory activity. The introduction of a phenyl group at the meta-position of the pyridine ring in 16a–16d showed subtle influences on the activity of their parent compounds. Compounds 17a and 17b were about 4-fold less active than 16a and 16b, but compound 17c was active as that of 16c. The sulphonamide 17d was not active. Therefore, the substitution of the thieno[3,2-c]pyrazol-3-amine with a sulphonyl group was not preferred.
Design, synthesis, and in vitro evaluation of aza-peptide aldehydes and ketones as novel and selective protease inhibitors
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2020
Thomas S. Corrigan, Leilani M. Lotti Diaz, Sarah E. Border, Steven C. Ratigan, Kayla Q. Kasper, Daniel Sojka, Pavla Fajtova, Conor R. Caffrey, Guy S. Salvesen, Craig A. McElroy, Christopher M. Hadad, Özlem Doğan Ekici
Initially, we proposed a methyl and a benzyl ketone to explore the tolerance of functional groups in the S1’ pocket where the ketone R’ group was anticipated to reside. We have chosen the methyl and benzyl groups for two reasons. (a) The methyl group is the smallest group possible for our proposed aza-peptide ketone design, and (b) the phenyl group, if tolerated, can be derivatised further to make more specific interactions at the prime site. Coupling of the warheads was performed by conversion of readily available pyruvic acid or phenylpyruvic acid to the corresponding acid chloride intermediates via reaction with oxalyl chloride, and then acyl substitution of the acid chloride with the aza-peptide hydrazide intermediates, thereby yielding the final aza-peptide ketones (Figure 4(B)). These two described methods were used for the synthesis of the aza-peptide aldehyde 3 as well as ketones 4 and 5, as shown in Figure 4(C).