15042-01-0Relevant articles and documents
Assessing the pKa-Dependent Activity of Hydroxyl Hydrogen Bond Donors in the Organocatalyzed Cycloaddition of Carbon Dioxide to Epoxides: Experimental and Theoretical Study
Yingcharoen, Prapussorn,Kongtes, Chutima,Arayachukiat, Sunatda,Suvarnapunya, Kittipong,Vummaleti, Sai V. C.,Wannakao, Sippakorn,Cavallo, Luigi,Poater, Albert,D' Elia, Valerio
, p. 366 - 373 (2019)
The development of hydrogen bond donors (HBDs) as catalytic moieties in the cycloaddition of carbon dioxide to epoxides is an active field of research to access efficient, inexpensive and sustainable metal-free systems for the conversion of carbon dioxide to useful chemicals. Thus far, no systematic attempt to correlate the activity of a diverse selection of HBDs to their physico-chemical properties has been undertaken. In this work, we investigate factors influencing the catalytic activity of hydroxyl HBDs from different chemical families under ambient conditions by considering the HBDs Br?nsted acidity (expressed as pKa), the number of hydroxyls and structural aspects. As an effect, this study highlights the crucial role of the hydroxyl protons’ Br?nsted acidity in determining the catalytic activity of the HBDs, identifies an ideal range for the hydroxyl HBDs proton acidity (9 a 11) and leads to a revaluation of phenol and to the discovery of a simple ascorbic acid derivative as efficient HBDs for the title cycloaddition reaction. Density functional theory (DFT) calculations show mild reactions barriers for the reaction catalysed by phenol and suggest the occurrence of aggregation between molecules of ascorbic acid as a further factor affecting catalytic activity. (Figure presented.).
Synthesis of new L-ascorbic ferulic acid hybrids
Voisin-Chiret, Anne Sophie,Bazin, Marc-Antoine,Lancelot, Jean-Charles,Rault, Sylvain
, p. 2533 - 2545 (2007)
A feasibility and chemical study of the coupling conditions of L-ascorbic acid with ferulic acid derivatives are described on the basis of the known synergistic effects of mixtures of various antioxidants. Novel L-ascorbic ferulic hybrids linked at the C-3 hydroxyl group were prepared with the aim to protect the alcohol function and the enediol system.
Design, synthesis, and neuroprotective effects of dual-brain targeting naproxen prodrug
Wang, Linhui,Zhang, Li,Zhao, Yi,Fu, Qiuyi,Xiao, Wenjiao,Lu, Runxin,Hai, Li,Guo, Li,Wu, Yong
, (2018)
A new dual-targeting naproxen prodrug conjugated with glucose and ascorbic acid for central nervous system (CNS) drug delivery was designed and synthesized in order to effectively deliver naproxen to the brain. Naproxen could be released from the prepared prodrugs when incubated with various buffers, mouse plasma, and brain homogenate. Also, the prodrug showed superior neuroprotective effect in vivo over naproxen. Our results suggest that chemical modification of therapeutics with warheads of glucose and ascorbic acid represents a promising and efficient strategy for the development of brain targeting prodrugs by utilizing the endogenous transportation mechanism of the warheads.
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Salomon
, p. 619 (1963)
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A New Convenient Method for the Synthesis of Chiral C3-Synthons
Emons, Carry H.H.,Kuster, Ben F.M.,Vekemans, Jozef A.J.M.,Sheldon, Roger A.
, p. 359 - 362 (1991)
Routes are described for the facile preparation of protected optically pure D- and L-glyceric acid (1a,b; 2a,b) starting from D-mannitol, D-isoascorbic acid and L-ascorbic acid.The key step is a ruthenium catalyzed oxidative cleavage of the vicinal diols 4a,b or the α-hydroxy acids 7a,b; 10a,b.
Site-Selective Photochemical Fluorination of Ketals: Unanticipated Outcomes in Selectivity and Stability
Capilato, Joseph N.,Pitts, Cody Ross,Rowshanpour, Rozhin,Dudding, Travis,Lectka, Thomas
, p. 2855 - 2864 (2020)
We report a method for the regioselective photochemical sp3 C-H fluorination of acetonide ketals that presents interesting problems in chemical reactivity. The question of why certain products of the reaction are stable while others are not is addressed, as is the question of why only select α-ethereal hydrogen atoms are targeted in the reaction. We demonstrate that the method can be employed to synthesize unprecedented fluorinated sugars and steroids, and it can also be applied toward the fluorination of carbamates. Though some substrates contain up to eight discrete α-ethereal C-H bonds, we observed site-selectivity in each case, prompting us to investigate potential transition states for the reaction. Finally, a remarkable regiochemical switch upon minor structural modification of a diketal is also analyzed.
Cyclohexyl Spiro-Fused α-Hydroxy Tetronic Acid Derivatives From Vitamin C
Poss, A. J.,Brodowski, M. H.
, p. 2505 - 2508 (1989)
The reaction of dienophile 4, prepared from L-ascorbic acid in 5 steps, with various dienes to prepare cyclohexyl spiro-fused α-hydroxy tetronic acid derivatives is reported.
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v. Vargha
, p. 847 (1932)
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Synthesis and Biological Evaluation of Ascorbyl-Conjugated Peptide Derivatives as Collagen Synthesis Stimulating Agents in Human Skin Fibroblasts
Park, Kyeong-Yong,Kim, Jiyeon
, p. 2449 - 2456 (2020)
Vitamin C (ascorbic acid) is a widely used agent for anti-aging and whitening in the field of cosmetics. It affects collagen production in skin cells, inhibits melanin synthesis, displays anti-oxidant activity, and improves the immune system. However, vitamin C has limitations in cell permeability and environmental condition such as heating and lighting decrease its stability. Thus, vitamin C derivatives are being developed to overcome these problems. In this study, we synthesized vitamin C derivatives with a succinoyl group at the 2-position and peptides in the form of ester bonds. We then evaluated the cytotoxicity and collagen synthesis activity of these new compounds in human skin fibroblasts. Vitamin C-conjugated peptides were also synthesized in ether and carbamate forms, and the optimal combination conditions of vitamin C and peptides were identified. In addition, collagen synthesis-stimulating activity of vitamin C-conjugated peptides was also evaluated and compared to the effects of vitamin C alone. Based on these results, we confirmed that the ester-bonded vitamin C-conjugated peptide GEKG showed more stimulating effect on the production of collagen and related gene expression than either vitamin C or GEKG alone. This study will provide important information for developing skin health products and other topical cosmetics using vitamin C and peptides.
Novel multifunctional ascorbic triazole derivatives for amyloidogenic pathway inhibition, anti-inflammation, and neuroprotection
Chauthong, Nattapong,Jiaranaikulwanitch, Jutamas,Jiranusornkul, Supat,Nilkosol, Supitcha,Pandith, Hataichanok,Tadtong, Sarin,Thammarat, Phanit,Vajragupta, Opa
supporting information, (2021/06/15)
Alzheimer’s disease (AD) is a common neurodegenerative disorder. The number of patients with AD is projected to reach 152 million by 2050. Donepezil, rivastigmine, galantamine, and memantine are the only four drugs currently approved by the United States Food and Drug Administration for AD treatment. However, these drugs can only alleviate AD symptoms. Thus, this research focuses on the discovery of novel lead compounds that possess multitarget regulation of AD etiopathology relating to amyloid cascade. The ascorbic acid structure has been designated as a core functional domain due to several characteristics, including antioxidant activities, amyloid aggregation inhibition, and the ability to be transported to the brain and neurons. Multifunctional ascorbic derivatives were synthesized by copper (I)-catalyzed azide–alkyne cycloaddition reaction (click chemistry). The in vitro and cell-based assays showed that compounds 2c and 5c exhibited prominent multifunctional activities as beta-secretase 1 inhibitors, amyloid aggregation inhibitors, and antioxidant, neuroprotectant, and anti-inflammatory agents. Significant changes in activities promoting neuroprotection and anti-inflammation were observed at a considerably low concentration at a nanomolar level. Moreover, an in silico study showed that compounds 2c and 5c were capable of being permeated across the blood–brain barrier by sodium-dependent vitamin C transporter-2.
Synthesis of l-ascorbic acid-amino acid-norcantharidin conjugates and their biological activity evaluation in vitro
Wang, Xianheng,Wu, Caoyuan,Zhang, Jidong,Zhao, Changkuo,Zhou, Yiqi
supporting information, (2022/01/06)
Three components of L-ascorbic acid, amino acid and functionalized norcantharidins were constructed together in several steps to form 42 norcantharidin derivatives in a high yield. The structure of these synthesized l-ascorbic acid-amino acid-norcantharidin conjugates are determined by 1HNMR, 13CNMR and MS spectrum. The results showed that compounds 6e, 6g, 6j, 6l, 6m, 6b, 6e, 6i, and 6n showed high cytotoxicity to HepG2 and compounds 6b, 6e-g, 6l, 6n, 7b, 7d, 7h, 7i, 7n, 8g, 8i exhibited high cytotoxicity to SW480; Meanwhile, besides 6b, 6e, 6g, and 6k, the other compounds showed less toxic to LO2 at a concentration of 50 μg/mg after 72 h. Compound 6g can induce Mφ-type macrophages derived from mouse bone marrow to polarize to M1-type macrophages.
Cosmetic composition having the effect of promoting collagen synthesis and inhibiting reactive oxygen species
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Paragraph 0068; 0103; 0106, (2021/06/22)
The present invention relates to a novel compound ascombi and its use for improving wrinkles.
