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Angewandte Chemie (International Ed. in... Oct 2019A palladium-catalyzed dearomative syn-1,4-oxyamination protocol using non-activated arenes has been developed. This one-pot procedure utilizes arenophile chemistry, and...
A palladium-catalyzed dearomative syn-1,4-oxyamination protocol using non-activated arenes has been developed. This one-pot procedure utilizes arenophile chemistry, and the corresponding para-cycloadducts are treated with oxygen nucleophiles via formal allylic substitution, providing direct access to syn-1,4-oxyaminated products. The reaction conditions permit a range of arenes, as well as different O-nucleophiles, such as oximes and benzyl alcohols. Moreover, this process was established in an asymmetric fashion, delivering products with high enantioselectivity. The dearomatized products are amenable to a multitude of further derivatizations ranging from olefin chemistry to C-H activation, giving rise to a diverse set of new functionalities. Overall, this dearomative functionalization offers rapid and controlled formation of molecular complexity, enabling straightforward access to functionalized small molecules from simple and readily available arenes.
Topics: Allyl Compounds; Amines; Catalysis; Cycloaddition Reaction; Molecular Structure; Oxygen; Palladium; Stereoisomerism
PubMed: 31482682
DOI: 10.1002/anie.201909838 -
Molecules (Basel, Switzerland) Jul 2020New chrysin-De-allyl-Pac-1 hybrid analogues, tethered with variable heterocyclic systems (-), were rationally designed and synthesized. The target compounds were...
New chrysin-De-allyl-Pac-1 hybrid analogues, tethered with variable heterocyclic systems (-), were rationally designed and synthesized. The target compounds were screened for in vitro antiproliferative efficacy in the triple-negative breast cancer (TNBC) cell line, MDA-MB-231, and normal human mammary epithelial cells (HMECs). Two compounds, and , had the highest efficacy and selectivity towards MDA-MB-231 cells, and thus, were further evaluated by mechanistic experiments. The results indicated that both compounds and induced apoptosis by (1) inducing cell cycle arrest at the G2 phase in MDA-MB-231 cells, and (2) activating the intrinsic apoptotic pathways in a concentration-dependent manner. Physicochemical characterizations of these compounds suggested that they can be further optimized as potential anticancer compounds for TNBC cells. Overall, our results suggest that and could be suitable leads for developing novel compounds to treat TNBC.
Topics: Allyl Compounds; Antineoplastic Agents; Apoptosis; Cell Cycle; Cell Movement; Cell Proliferation; Female; Flavonoids; Humans; Hydrazones; Piperazines; Triple Negative Breast Neoplasms; Tumor Cells, Cultured
PubMed: 32635530
DOI: 10.3390/molecules25133063 -
Phytotherapy Research : PTR Mar 2024Cancer is a highly heterogeneous disease that poses a serious threat to human health worldwide. Despite significant advances in the diagnosis and treatment of cancer,... (Review)
Review
Cancer is a highly heterogeneous disease that poses a serious threat to human health worldwide. Despite significant advances in the diagnosis and treatment of cancer, the prognosis and survival rate of cancer remain poor due to late diagnosis, drug resistance, and adverse reactions. Therefore, it is very necessary to study the development mechanism of cancer and formulate effective therapeutic interventions. As widely available bioactive substances, natural products have shown obvious anticancer potential, especially by targeting abnormal epigenetic changes. The main active part of garlic is organic sulfur compounds, of which diallyl trisulfide (DATS) content is the highest, accounting for more than 40% of the total composition. The garlic-derived compounds have been recognized as an antioxidant for cancer prevention and treatment. However, the molecular mechanism of the antitumor effect of garlic-derived compounds remains unclear. Recent studies have identified garlic-derived compound DATS that plays critical roles in enhancing CpG demethylation or promoting histone acetylation as an epigenetic inhibitor. Here, we review the therapeutic progress of garlic-derived compounds against cancer through epigenetic pathways.
Topics: Humans; Garlic; Antioxidants; Apoptosis; Sulfides; Neoplasms; Allyl Compounds; Biological Products
PubMed: 38194996
DOI: 10.1002/ptr.8108 -
Acta Tropica Nov 2022Hymenolepis nana, a parasitic tapeworm distributed worldwide, is very prevalent in countries with poor sanitary conditions. Garlic is widely used as a seasoning and...
Hymenolepis nana, a parasitic tapeworm distributed worldwide, is very prevalent in countries with poor sanitary conditions. Garlic is widely used as a seasoning and medicinal plant all over the world, and its derivatives have proven anti-microbial and anti-inflammatory effects. Our study explored the cestocidal and therapeutic effects of allicin derivatives against H. nana in vitro and in vivo. Worms taken from a host were cultured in vitro, and the effects of allyl sulfide (DAS), allyl disulfide (DADS) and dimethyl sulfoxide (DMSO) treatments were observed. Male BALB/c mice were then fed eggs to produce infection, given drugs for ten days and dissected. The results of this study showed that DADS in garlic exhibited good cestocidal effects in vitro and in vivo. DADS and DATS reduced motility, induced mortality and damaged body segments of worms in vitro. In vivo, the number of worms in the low-dose and high-dose DADS groups was significantly less than the infected control group. DADS effected cytokine changes in BALB/c mice after infection. IFN-γ increased, IL-2, 4, 6 and 13 decreased, and IL-5, 10 and IL-12 p70 did not change significantly. As a medicinal plant, garlic has many active ingredients that can developed as anti-microbial or parasite-related drugs.
Topics: Allyl Compounds; Animals; Antioxidants; Cytokines; Garlic; Hymenolepis nana; Mice; Mice, Inbred BALB C; Sulfides
PubMed: 35908577
DOI: 10.1016/j.actatropica.2022.106580 -
Journal of Nutritional Science and... 2015Lifestyle-related diseases have complex pathogenesis which consists of several different steps. Basic causes of the diseases are attributed to unhealthy lifestyles in... (Review)
Review
Lifestyle-related diseases have complex pathogenesis which consists of several different steps. Basic causes of the diseases are attributed to unhealthy lifestyles in dietary habits, physical activity and suffering stress. The unhealthy lifestyles induce risk factors such as hypertension, dyslipidemia, obesity, and hyperglycemia. These risk factors all promote arteriosclerosis leading to serious vascular complications (i.e., thrombotic diseases), myocardial infarction and cerebral infarction. The total number of deaths from these thrombotic diseases almost equals that from cancer in our country. Cancer is also a typical lifestyle-related disease. Food has three different functions: the primary function is to provide enough nutrients to meet the metabolic requirements. The secondary function is the one relating to food preference. The third function is to control our body functions, which help reduction of the risk of diseases. Some of the compounds derived from food, especially phytochemicals in edible plants, vegetables and herbs, have potent functions to control our body functions and contribute to promoting our health. In this review article, we overview the lifestyle-related diseases and food functions involving prevention and amelioration of the diseases by food components especially from edible plants and vegetables. As an example, we will describe the food function of garlic and the prevention of lifestyle-related diseases by its components. Allyl sulfides are characteristic flavor compounds derived from garlic, and these organosulfur compounds are responsible for the food function of garlic.
Topics: Allyl Compounds; Antioxidants; Cardiovascular Diseases; Garlic; Humans; Life Style; Sulfides; Sulfur Compounds; Vegetables
PubMed: 26598900
DOI: 10.3177/jnsv.61.S83 -
Anti-cancer Agents in Medicinal... 2019Cancer is a multi-factorial disease including alterations in the cell signalling pathways. Currently, several drugs are in use to treat cancer but such drugs show... (Review)
Review
BACKGROUND
Cancer is a multi-factorial disease including alterations in the cell signalling pathways. Currently, several drugs are in use to treat cancer but such drugs show negative side effects on normal cells and cause severe toxicity.
METHODS
The current research is mainly focused on medicinal plants with potential therapeutic efficacy in the treatment of cancer without any adverse effects on normal cells. In this regard, garlic and its active compounds including diallyl sulfide, diallyl trisulfide, ajoene, and allicin have been established to suppress the growth of cancer and killing of cancer cells.
RESULT
The review focuses on garlic and its active compounds chemopreventive effect through modulating various cell signalling pathways. Additionally, garlic and its active compound were established to induce cell cycle arrest at the G0/G1 phase and G2/M phases in cancer cells, increase the expression of tumor suppressor genes, inhibit the angiogenesis process, induction of apoptosis and modulation of various other genetic pathways.
CONCLUSION
This review sketches the diverse chemopreventive activities of garlic and their active ingredients in the management of cancer mainly focusing on cell signalling pathways.
Topics: Allyl Compounds; Cell Proliferation; Disulfides; Garlic; Humans; Neoplasms; Plants, Medicinal; Signal Transduction; Sulfides; Sulfinic Acids; Sulfoxides
PubMed: 30963982
DOI: 10.2174/1871520619666190409100955 -
The Journal of Organic Chemistry Nov 2022Cobalt(III)-catalyzed allylation of 1,3-dicarbonyl compounds has been reported with in situ generated allyl reagents from alkenes and dimethyl sulfoxide (DMSO). This...
Cobalt(III)-catalyzed allylation of 1,3-dicarbonyl compounds has been reported with in situ generated allyl reagents from alkenes and dimethyl sulfoxide (DMSO). This novel protocol enables a high regio- and stereoselective access for a broad range of allyl 1,3-dicarbonyl compounds. In the transformation, DMSO plays the role of a C1 source, and it incorporates with alkenes to form the allyl reagent allylic methyl thioether. Moreover, a multiple-step pathway has been proposed to rationalize the mechanism study, which involves silver-mediated coupling, Co(III)-catalyzed π-allylation, and intermolecular nucleophilic substitution.
Topics: Alkenes; Dimethyl Sulfoxide; Allyl Compounds; Cobalt; Catalysis; Stereoisomerism; Indicators and Reagents
PubMed: 36263891
DOI: 10.1021/acs.joc.2c01796 -
International Journal of Molecular... Jul 2017Bioactive dietary agents have been shown to regulate multiple cancer hallmark pathways. Epidemiologic studies have linked consumption of vegetables, such as garlic and... (Review)
Review
Bioactive dietary agents have been shown to regulate multiple cancer hallmark pathways. Epidemiologic studies have linked consumption of vegetables, such as garlic and onions, to decreased incidence of cancer. Diallyl trisulfide (DATS), a bioactive compound derived from vegetables, has been investigated as an anti-cancer and chemopreventive agent. Preclinical studies provide ample evidence that DATS regulates multiple cancer hallmark pathways including cell cycle, apoptosis, angiogenesis, invasion, and metastasis. DATS has been shown to arrest cancer cells at multiple stages of the cell cycle with the G2/M arrest being the most widely reported. Additionally, increased pro-apoptotic capacity as a result of regulating intrinsic and extrinsic apoptotic pathway components has been widely reported following DATS treatment. Invasion, migration, and angiogenesis represent emerging targets of DATS and support its anti-cancer properties. This review summarizes DATS mechanisms of action as an anti-cancer and chemopreventive agent. These studies provide rationale for future investigation into its use as a cancer chemopreventive agent.
Topics: Allium; Allyl Compounds; Animal Experimentation; Animals; Apoptosis; Biosynthetic Pathways; Cell Cycle; Cell Movement; Chemoprevention; Clinical Trials as Topic; Dietary Supplements; Hormones; Humans; Neoplasms; Plant Extracts; Signal Transduction; Sulfides; Treatment Outcome
PubMed: 28788092
DOI: 10.3390/ijms18081645 -
Organic Letters Oct 2022Herein, we report the first asymmetric total synthesis of iheyamine B from 2,2'-bisindoloazepinone using the stereoselective construction of the -vicinal 2-oxopropyl...
Herein, we report the first asymmetric total synthesis of iheyamine B from 2,2'-bisindoloazepinone using the stereoselective construction of the -vicinal 2-oxopropyl moiety in the azepine scaffold. The asymmetric decarboxylative allylic alkylation provided the α-allylated 2,2'-bisindoloazepinone intermediate. The subsequent conversion of the lactam moiety into another allyl group in a -selective manner followed by Wacker oxidation of each allyl unit to the corresponding 2-oxopropyl group completed the total synthesis of iheyamine B.
Topics: Alkylation; Allyl Compounds; Azepines; Catalysis; Lactams; Palladium; Stereoisomerism
PubMed: 36169573
DOI: 10.1021/acs.orglett.2c02788 -
Advances in Experimental Medicine and... 2016Diallyl sulfide (CHS, DAS) is one of the novel natural organosulfur compounds, which is mostly obtained from the genus Allium plants. Numerous studies have revealed... (Review)
Review
Diallyl sulfide (CHS, DAS) is one of the novel natural organosulfur compounds, which is mostly obtained from the genus Allium plants. Numerous studies have revealed several unique properties of DAS in terms of its health-promoting effects. DAS has proved to be anticancer, antimicrobial, anti-angiogenic, and immunomodulatory like unique functions as demonstrated by the multiple investigations. Diallyl sulfide can also impede oxidative stress and chronic inflammation as suggested by the literature. Studies also explored that DAS could thwart the development of chronic diseases like cancer, neuronal, cardiovascular disease through modulating mechanistic pathways involved in pathogenesis. In this book chapter, we have attempted to give the comprehensive view on DAS about the physiochemical and biological properties, and its preventive role in chronic diseases with a mechanistic overview.
Topics: Allium; Allyl Compounds; Animals; Anti-Inflammatory Agents; Antineoplastic Agents, Phytogenic; Antioxidants; Chronic Disease; Drug Discovery; Humans; Phytotherapy; Plants, Medicinal; Signal Transduction; Sulfides
PubMed: 27771923
DOI: 10.1007/978-3-319-41342-6_6