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Monographs of fragrance chemicals and extracts that have caused contact allergy / allergic contact dermatitis
Published in Anton C. de Groot, Monographs in Contact Allergy, 2021
3-Methyl-5-(2,2,3-trimethyl-3-cyclopentenyl)pent-4-en-2-ol is a colorless to pale yellow clear liquid; its odor type is woody and its odor at 10% in dipropylene glycol is described as ‘sandalwood woody musk’ (www.thegoodscentscompany.com). 3-Methyl-5-(2,2,3-trimethyl-3-cyclopentenyl)pent-4-en-2-ol is a synthetic chemical, not found in nature (and consequently not in essential oils (5)).
Design of Bioresponsive Polymers
Published in Deepa H. Patel, Bioresponsive Polymers, 2020
Anita Patel, Jayvadan K. Patel, Deepa H. Patel
Industrially imperative products can be produced by the ROMP technique that is a kind of olefin metathesis chain-growth polymerization. The liberation of ring strain in cyclic olefins like cyclopentene or else norbornene is the instigator of the reaction and a broad variety of catalysts has been found.
Disposition and Metabolism of Drugs of Dependence
Published in S.J. Mulé, Henry Brill, Chemical and Biological Aspects of Drug Dependence, 2019
Studies on structure-activity relationship in barbiturates have provided some generalizations: (a) substitution of both hydrogen atoms on C(5) was an essential requisite for activity; (b) substitution with phenyl group on C(5) conferred anticonvulsant properties in compounds; (c) increase in length of alkyl side chains on C(5) to five or six carbon atoms increased depressant action and larger carbon chains produced stimulant activity; (d) branched chains on C(5) produced long-acting barbiturates and substitution of cyclopentenyl or cyclohexenyl groups on C(5) resulted in short-acting compounds; (e) unsatura-tion in side chains on C(5) enhanced depressant properties; and (f) substitution of S atom in place of 0 at 2-position produced short-acting barbiturates. The names and chemical structures of different barbiturates are given in Table 1.
Protein tyrosine phosphatase 1B (PTP1B) inhibitors as potential anti-diabetes agents: patent review (2015-2018)
Published in Expert Opinion on Therapeutic Patents, 2019
Hidayat Hussain, Ivan R Green, Ghulam Abbas, Sergazy M Adekenov, Wahid Hussain, Iftikhar Ali
The Laurencia genus of red algae is famous for biosynthesizing a diverse range of metabolites representing an astonishing chemical diversity. These metabolites include diterpenes, C15-acetogenins, halogenated sesquiterpenes, and triterpenes which all showed a diverse range of biological effects viz., antihelmintic, antifeedant, antimicrobial, antifouling and cytotoxic effects [40,41]. Laurane-type sesquiterpenes 61–65 (Figure 5) were reported from Laurencia okamurai and their structures were determined by using extensive spectroscopic techniques [42]. Sesquiterpenes 61–65 possess PTP1B inhibitory effects with IC50 ranging from 4.9 to 14.9 μg/mL. Among these compounds, sesquiterpenes 64 and 65 showed activity with IC50 of 4.9 and 7.0 μg/mL respectively. On the other hand the activities of compounds 61 (IC50: 14.9 μg/mL) and 62 (IC50: 13.0 μg/mL) having the hydroperoxy moiety at C-3 of the cyclopentenyl group were not impressive. In another patent, two sesquiterpenes named beshanzuenones C (66) and D (67) were reported from Abies beshanzuensis and it was demonstrated that these compounds have an uncommon [6/6/5]-fused tricyclic ring system [43]. Interstingly, various species of the genus Abies are used to treat stomachache, colds, rheumatic diseases, indigestion, and pulmonary diseases in Korean folk medicine. Moreover sesquiterpenes 66 and 67 possess PTP1B inhibitory effects with IC50 values of 16.6 and 10.6 μg/mL respectively.
Synthesis, antiasthmatic, and insecticidal/antifungal activities of allosamidins
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2019
Gangliang Huang, Hualiang Huang
The regio- and stereocontrolled total synthesis of (-)-allosamizoline 2 was studied (Scheme 1)48. Using D-glucosamine as raw material, aldehyde 3 was synthesized by five-step reaction. The Wittig olefination of aldehyde 3 was carried out by using ylide Ph3P = CHCO2Me to obtain a high yield (91%) of acrylate 4. In the ring-closed metathesis reaction, the terminal substituent of the alkene was not transferred to the cyclized product. The ring-closing metathesis also took place smoothly and cyclopentene 5 was obtained in 88% yield. The key steps of the synthesis included halogen cyclization to provide oxazoline ring, followed by stereoselective addition of alkene radical, and finally carried out alkene isomerization to form hydroxymethyl. (-)-Allosamizoline 2 was prepared by 13-step reaction with an overall yield of 22%.
HDAC inhibitors: a 2013–2017 patent survey
Published in Expert Opinion on Therapeutic Patents, 2018
Micaela Faria Freitas, Muriel Cuendet, Philippe Bertrand
The activities of compounds 45–52, which are mainly HDAC4 inhibitors, are reported in Table 3. The group of Dominguez et al. investigated several scaffolds to design HDAC inhibitors, focusing on hydroxamic acids linked to a hindered carbon (tertiary, quaternary). Diarylhydroxyacetamides 45 (Scheme 3(g)) [38] were synthesized in a straightforward manner, with modulation of the biaryl part. Aryl substituted cyclopropyl hydroxamates 46–49 were also proposed (Scheme 3(h)) [39]. Compounds with a quaternary carbon bearing two rings and the hydroxamic acid function were investigated and are illustrated by compound 50 (Scheme 3(i)) [40]. An enantiomeric resolution of the intermediate ketone is described. An analogous series was proposed with a quaternary carbon included in a cyclopentene ring [41]. The chemistry used the same ketone intermediate to obtain compounds such as 51 or 52 (Scheme 3(i)).