Synthesis and Evaluation of Octocrylene-Inspired Compounds for Uv-Filter Activity

Polonini, Hudson; Lopes, Rosangela S.; Beatriz, Adilson; Gomes, Roberto da Silva; Silva, Adriano O.; Lima, Ricardo Vieira de; Nunes, Gláucia. A.; Brandão, Marcos Antônio Fernandes; Raposo, Nádia Rezende Barbosa; Lima, Dênis Pires de

doi:10.5935/0100-4042.20140160

Cited by 6 publications

(11 citation statements)

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“…Wavelength at which the integral of the spectral absorbance curve reaches 90% of the area under the curve from 290 to 400 nm The SPF value of the hydrazones 3noticeable when compared to the commercial PBSA filter, used as a reference. In general, the values obtained are in agreement with what has been reported in the literature on sunscreen filters that present phenyl rings: the presence of 4-methoxy, 2-hydroxy or 4hydroxy groups increases the filtering capacity[42]. Hydrazones 3 and 6 showed the same protection value, despite the different number and position of hydroxyl groups on the benzylidene ring.…”

supporting

confidence: 90%

Benzofuran hydrazones as potential scaffold in the development of multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity

Baldisserotto

Demurtas

Lampronti

et al. 2018

European Journal of Medicinal Chemistry

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New benzofuranhydrazones 3-12 were easily prepared and assayed for their radical-scavenging ability. Hydrazones 3-12 showed different extent antioxidant activity in DPPH, FRAP and ORAC assays. Good antioxidant activity is related to the number and position of hydroxyl groups on the arylidene moiety. High antioxidant activity is showed by the 2-hydroxy-4-(diethylamino)benzylidene derivative 11. Furthermore, hydrazones 3-12 showed photoprotective capacities with satisfactory in vitro SPF as compared to the commercial PBSA sunscreen filter. The antiproliferative effects of the hydrazones 3-12 was tested on erythroleukemia K562 and Colo-38 melanoma human cells. All the compounds showed growth inhibition in the micromolar to sub micromolar concentration range. If taken together these results points to benzofuran hydrazones as potential multifunctional molecules especially in the treatment of neoplastic diseases being the good antioxidant properties of 5, 7 and 11 correlated to their high antiproliferative activity.

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supporting

confidence: 90%

Benzofuran hydrazones as potential scaffold in the development of multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity

Baldisserotto

Demurtas

Lampronti

et al. 2018

European Journal of Medicinal Chemistry

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“…Interestingly, compound 21 had a lower value than 7 ( p ‐methoxy substituent on the 8‐phenyl ring), indicating that a p ‐methoxy group is better than hydroxy. Compounds 29 and 28 have two hydroxy groups at positions 3 and 5, and 2 and 5, respectively; they have lower SPF values, in agreement with the fact that UV filters based on phenyl moieties are ortho and para substituted . However, compounds 19 and 31 have the same value of protection despite the presence of p ‐hydroxy and m ‐methoxy, and p ‐hydroxy groups on the phenyl ring, respectively.…”

Section: Resultsmentioning

confidence: 53%

A Multitarget Approach toward the Development of 8‐Substituted Purines for Photoprotection and Prevention of UV‐Related Damage

et al. 2017

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Ultraviolet (UV) light is the most abundant and significant modifiable risk factor for skin cancer and many other skin diseases such as early photo-aging. Across the solar radiation spectrum, UV light is the main cause behind skin problems. In the search for novel photoprotective compounds, a new series of 8-substituted purines were synthesized from commercially available 6-hydroxy-4,5-diaminopyrimidine hemisulfate or 4,5-diaminopyrimidine. All title compounds were investigated for their UV filtering, antioxidant, antifungal, and antiproliferative activities. For the photoprotection assays we used a diffuse transmittance technique to determine the sun protection factor (SPF) in vitro, and 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric ion reducing antioxidant power (FRAP) tests for evaluating the antioxidant activity of the more potent compounds. Among them, 8-(2,5-dihydroxyphenyl)-7H-purin-6-ol (compound 26) proved to be a good radical scavenger and is also endowed with broad-spectrum UVA filtering capabilities, suitable for further development as a protective molecule.

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“…The compounds shown in Figure were synthesized according to a described procedure . Reaction with ethyl cyanoacetate furnishes only the 1 E isomer, and the 1 Z isomer has to be obtained from UV‐induced isomerization under presence of (−)‐riboflavin .…”

Section: Methodsmentioning

confidence: 99%

Unexpected behavior of the ³J_CH coupling constant in unsaturated compounds

Couto

Navarro‐Vázquez

Tormena

2019

Magnetic Reson in Chemistry

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The experimental and theoretical behavior of the (OC)CCH 3JCH coupling constant is investigated for a series of α,β‐unsaturated compounds (1 to 8), and for some of them, the well‐known relationship (3JCHcis < 3JCHtrans) was observed. However, for some compounds, close values for 3JCHcis and 3JCHtrans couplings were observed, and for aldehydes group containing compounds (7 and 8E), an inversion order is observed (3JCHcis > 3JCHtrans). In all cases where the 3JCHcis < 3JCHtrans relationship it is not followed, a polar group or electronegative atom oriented in opposite direction (s‐trans) to the HCC hydrogen is present, suggesting that conformational preference of such polar group or atoms are important factor on the behavior of 3JCH couplings. Taking all of these in consideration, a new Karplus‐type equation was proposed for 3JCH couplings in α,β‐unsaturated compounds, which can be used for configurational and conformational assignment on trisubstituted double bond derivatives.

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Synthesis and Evaluation of Octocrylene-Inspired Compounds for Uv-Filter Activity

Cited by 6 publications

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Benzofuran hydrazones as potential scaffold in the development of multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity

Benzofuran hydrazones as potential scaffold in the development of multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity

A Multitarget Approach toward the Development of 8‐Substituted Purines for Photoprotection and Prevention of UV‐Related Damage

Unexpected behavior of the ³J_CH coupling constant in unsaturated compounds

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Synthesis and Evaluation of Octocrylene-Inspired Compounds for Uv-Filter Activity

Cited by 6 publications

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Benzofuran hydrazones as potential scaffold in the development of multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity

Benzofuran hydrazones as potential scaffold in the development of multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity

A Multitarget Approach toward the Development of 8‐Substituted Purines for Photoprotection and Prevention of UV‐Related Damage

Unexpected behavior of the 3JCH coupling constant in unsaturated compounds

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Unexpected behavior of the ³J_CH coupling constant in unsaturated compounds