1802-16-0Relevant academic research and scientific papers
Three novel anti-microfouling nitroalkyl pyridine alkaloids from the Okinawan marine sponge Callyspongia sp
Wang, Gui-Yang-Sheng,Kuramoto, Makoto,Uemura, Daisuke,Yamada, Akihiro,Yamaguchi, Kaori,Yazawa, Kazunaga
, p. 1813 - 1816 (1996)
Three novel nitroalkyl pyridine alkaloids, untenines A, B and C, with anti-microfouling activity, were first isolated from the Okinawan marine sponge Callyspongia sp. Their structures were elucidated on the basis of spectroscopic methods. The synthesis of
Synthetic 3-alkylpyridine alkaloid analogues as a new scaffold against leukemic cell lines: cytotoxic evaluation and mode of action
Evangelista, Fernanda Cristina Gontijo,de Freitas Lopes, Aline,Andrade, Silmara Nunes,de Souza Barbosa, Camila,da Silva, Julia Dias,Neves, Alessandra Mirtes Marques,de Mello Gomide Loures, Cristina,Brito, Larissa Froede,de Sousa, Lirlandia Pires,Borges, Karina Braga Gomes,Viana, Gustavo Henrique Ribeiro,de Pilla Varotti, Fernando,de Paula Sabino, Adriano
, p. 1567 - 1578 (2019)
Leukemia is a malignant disease that originates in the bone marrow, local of blood cells production. Chemotherapy treatment is one of the alternatives to improve the survival of patients. In this context, the search for new compounds with potential cytotoxic action is justified. The present work evaluated the cytotoxic activity of 16 new synthetic analogs of 3-alkylpyridine alkaloids. The cytotoxic profiles were determined by MTT in vitro assay against THP-1 (acute monocytic leukemia), K562 (chronic myeloid leukemia) and PBMC (peripheral blood mononuclear) human cells. To investigate the mechanism of action, cell cycle analysis and alterations of TP53, p21, Bax, Bcl2, NOX-1, NOX-2, NOX-4 and p47-phox gene expressions were performed by qPCR, along with the measurement of reactive oxygen species (2’,7’-dichlorodihydrofluorescein diacetate and dihydroethidium). Compounds 4c, 5b, 5c and 6d were the most active and selective for THP-1 and compounds 7c and 11 were found to be more active for K562. All of this induced apoptosis in the tested strains. Concerning the investigation of the mechanism of action, it was observed that the pathway being activated is a p53-independent pathway. The data presented in this work indicate that 3-alkylpyridine alkaloid analogues are a potential class of compounds with cytotoxic action.
A biomimetic approach to the manzamine alkaloids
Baldwin, Jack E.,Claridge, Tim D. W.,Culshaw, Andrew J.,Heupel, Florian A.,Smrckova, Svatava,Whitehead, Roger C.
, p. 6919 - 6922 (1996)
Results from model studies of a synthetic approach to the manzamine alkaloids based on a biogenetic theory are reported together with the synthesis of a plausible biogenetic precursor to these alkaloids.
ECTONUCLEOTIDE PYROPHOSPHATASE/PHOSPHODIESTERASE 1 (ENPP1) MODULATORS AND USES THEREOF
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Paragraph 00606; 00645, (2021/07/02)
Provided herein are small molecule modulators of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.
Synthesis and BK channel-opening activity of 2-amino-1,3-thiazole derivatives
Cui, Yong-Mei,Ji, Tong-Tong,Jo, Heeji,Lin, Hai-Xia,Park, Chul-Seung,Qi, Xiao-Lei,Wang, Xue-Ying
supporting information, (2021/05/19)
A series of 2-amino-5-arylmethyl- or 5-heteroarylmethyl-1,3-thiazole derivatives were synthesized and evaluated for BK channel-opening activities in cell-based fluorescence assay and electrophysiological recording. The assay results indicated that the activities of the investigated compounds were influenced by the physicochemical properties of the substituent at benzene ring.
Transition-Metal- A nd Light-Free Directed Amination of Remote Unactivated C(sp3)-H Bonds of Alcohols
Kurandina, Daria,Yadagiri, Dongari,Rivas, Monica,Kavun, Aleksei,Chuentragool, Padon,Hayama, Keiichi,Gevorgyan, Vladimir
supporting information, p. 8104 - 8109 (2019/06/13)
Due to the great value of amino alcohols, new methods for their synthesis are in high demand. Abundant aliphatic alcohols represent the ideal feedstock for the method development toward this important motif. To date, transition-metal-catalyzed approaches for the directed remote amination of alcohols have been well established. Yet, they have certain disadvantages such as the use of expensive catalysts and limited scope. Very recently, transition-metal-free visible-light-induced radical approaches have emerged as new powerful tools for directed remote amination of alcohols. Relying on 1,5-HAT reactivity, these methods are limited to β-or δ- A mination only. Herein, we report a novel transitionmetal- A nd visible-light-free room-temperature radical approach for remote β-, γ-, and δ-C(sp3)-N bond formation in aliphatic alcohols using mild basic conditions and readily available diazonium salt reagents.
Synthesis and antitumor activity of novel pyridinium fullerene derivatives
Yasuno, Takumi,Ohe, Tomoyuki,Ikeda, Hitomi,Takahashi, Kyoko,Nakamura, Shigeo,Mashino, Tadahiko
, p. 6325 - 6337 (2019/08/28)
Purpose: We have previously reported that some cationic fullerene derivatives exhibited anticancer activity, and they are expected to be a potential lead compound for an anti-drug resistant cancer agent. However, they are bis-adducts and a mixture of multiple regioisomers, which cannot be readily separated due to the variability of substituent positions on the fullerene cage. To overcome this issue, we evaluated the antiproliferative activities of a set of mono-adduct derivatives and examined their structure-activity relationship. In addition, the in vivo antitumor activity of selected derivatives was also examined. Methods: Nineteen pyridinium fullerene derivatives were newly designed and synthesized in this study. Their antiproliferative activities were evaluated using several cancer cell lines including drug-resistant cells. Furthermore, in vivo antitumor activity of several derivatives was investigated in mouse xenograft model of human lung cancer. Results: The derivatives inhibited the proliferation of cancer cell lines, including cisplatin-resistant cells and doxorubicin-resistant cells. It was also shown that compound 10 (10 μM), 13 (10 μM) and cis-14 (10 μM) induced the intracellular oxidative stress. In addition, compound 13 (20 mg/kg) and cis-14 (15 mg/kg) significantly exhibited antitumor activity in mouse xenograft model of human lung cancer. Conclusion: We synthesized a novel set of mono-adduct fullerene derivatives functionalized with pyridinium groups and found that most of them show potent antiproliferative activities against cancer cell lines and some of them show significant antitumor activities in vivo. We propose that these fullerene derivatives serve as the lead compounds for a novel type of antitumor agents.
Synthesis and biological evaluation of aminothiazoles against Histoplasma capsulatum and Cryptococcus neoformans
Ishita, Keisuke,Stefanopoulos, Stavros,Khalil, Ahmed,Cheng, Xiaolin,Tjarks, Werner,Rappleye, Chad A.
, p. 2251 - 2261 (2018/03/29)
The design and synthesis of a library of forty novel 2-aminoazole analogues as well as their evaluation as antifungal compounds against Histoplasma capsulatum and Cryptococcus neoformans is described. These structures were derived from N-[5-(1-naphthaleny
Synthesis of β-heteroaryl carbonyl compounds via direct cross-coupling of allyl alcohols with heteroaryl boronic acids under cooperative bimetallic catalysis
Zhu, Mingxiang,Du, Hongli,Li, Jingya,Zou, Dapeng,Wu, Yusheng,Wu, Yangjie
, p. 1352 - 1355 (2018/03/06)
The eco-friendly cooperative Cu/Pd-catalyzed oxidative Heck reaction of allyl alcohols with heteroaryl boronic acids under air was described. The ready availability of starting materials and the mild reaction conditions made this protocol a safe and operationally convenient strategy for the efficient synthesis of β-heteroaryl carbonyl compounds.
NRF2 REGULATORS
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Page/Page column 418; 419, (2015/07/07)
The present invention relates to bis aryl analogs, pharmaceutical compositions containing them and their use as Nrf2 regulators.
