Article
Chemistry, Multidisciplinary
Ivan Mosiagin, Anthony J. Fernandes, Alena Budinska, Liana Hayriyan, Kai E. O. Ylijoki, Dmitry Katayev
Summary: This study reports an efficient, mild, and catalytic ipso-nitration method of organotrimethylsilanes using an electrophilic N-nitrosaccharin reagent. The method allows chemo-selective nitration under mild reaction conditions and exhibits remarkable substrate generality and functional group compatibility. The reaction conditions are orthogonal to other common functionalities, allowing programming of molecular complexity via successive transformations or late-stage nitration. Detailed mechanistic investigation supports a classical electrophilic aromatic substitution mechanism.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Fuqiang Jia, Ao Li, Xiangdong Hu
Summary: The development of a new N-nitro type compound, dinitro-5,5-dimethylhydantoin (DNDMH), as an arenenitration reagent has been reported. The study demonstrated that arene nitration with DNDMH showed good tolerance towards diverse functional groups. Interestingly, only the N-nitro unit on N1 of DNDMH was delivered to the nitroarene products, while the N-nitro type compound with a single N-nitro unit on N2 could not promote the arene nitration reaction.
Article
Chemistry, Medicinal
Tanner J. Schumacher, Naresh Sah, Komaraiah Palle, Jon Rumbley, Venkatram R. Mereddy
Summary: This work describes the synthesis and evaluation of potential anticancer agents, substituted benzofuran piperazines. The synthesized candidates were tested for their ability to inhibit cell proliferation in six different cancer cell lines. Furthermore, in vitro and in vivo evaluations revealed the lead compound's potential pathways for causing cell death and its effective anticancer efficacy in a MDA-MB-231 xenograft model.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2023)
Review
Oncology
Masa Brumec, Monika Sobocan, Iztok Takac, Darja Arko
Summary: Triple-negative breast cancer lacks hormone receptors and HER2 amplifications, posing challenges in treatment selection. However, some TNBCs express androgen receptor (AR) which can be a therapeutic target. This review summarizes clinical features and potential therapies for AR-positive TNBC and highlights the need for further research on AR signaling pathways.
Review
Chemistry, Organic
Beatrice Quiclet-Sire, Samir Z. Zard
Summary: This article summarizes the routes to tetralones, tetralines, and naphthalenes based on the xanthate chemistry developed in the authors' laboratory. The reversible transfer of xanthates allows radical additions to unactivated alkenes and tolerates a wide range of functional groups, including common polar groups. Xanthates also enable radical ring closures onto aromatic rings, offering a convergent approach to building blocks relevant to pharmaceutical, agrochemical, and material sciences.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Guoqiang An, Limin Wang, Jianwei Han
Summary: This method developed by using palladium-catalyzed C-2-arylation/intramolecular acylation with arylcarboxylic acids using diaryliodonium salts has the advantage of good step-economy by two chemical bonds formation in one pot.
Article
Chemistry, Medicinal
Xiujin Chang, Di Zhang, Fangui Qu, Youquan Xie, Tian Chen, Yuqing Zhang, Qianming Du, Jinlei Bian, Zhiyu Li, Jubo Wang, Xi Xu
Summary: Prostate cancer (PC) is a common cancer in men, and androgen receptor (AR) is a validated drug target for PC treatment. However, PC often becomes resistant to AR antagonists, so there is a need for novel drugs. A new AR antagonist, molecule 26h, was discovered with improved antagonistic activity and potent degradation of AR. It also blocks AR nuclear translocation and inhibits AR/AR-V7 heterodimerization, leading to inhibition of gene transcription. In xenograft models, 26h showed potent efficacy against PC.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Sudip Sau, Prasenjit Mal
Summary: A convenient one-pot synthesis of quinoxaline-2,3-dione has been achieved by C-H hydroxylation of quinoxalin-2(1H)-one using TBN as a promoter of the reaction in DMSO. First, radical-mediated nitration using TBN at C-3 of quinoxalin-2(1H)-one was carried out, followed by hydroxylation with water via ipso-substitution to obtain quinoxaline-2,3-dione.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Hannah R. Manion-Sommerhalter, Dmytro Fedoseyenko, Sumedh Joshi, Tadhg P. Begley
Summary: A chemoenzymatic synthesis method was described, which achieved yield enhancement by using different reducing agents and a fluorinated analogue. This synthesis route revealed the mechanism of the MqnD-catalyzed reaction.
Article
Chemistry, Medicinal
Kotaro Ochiai, Shinya Fujii
Summary: Ferrocene, a representative organometallic compound, has high stability and hydrophobicity, making it suitable for drug research. Nitro- and cyanophenylferrocene derivatives exhibit activity as androgen receptor antagonists. The developed compound, 3-nitrophenylferrocene, shows potential as an AR antagonist.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Nguyen Van Trang, Phan Thi Thuy, Dinh Thi Mai Thanh, Ninh The Son
Summary: The antioxidative activities of the original compound dehydro-delta-viniferin and its three derivatives were extensively studied using density functional theory calculations. The O-H bond breakage is found to be responsible for the antioxidative activity, influenced by the environment. Different solvents show different antioxidative routes, with compound 3 being the best antioxidative agent due to its planar structure.
Article
Pharmacology & Pharmacy
Yun-Ho Choi, Jaeyoon Kim, Jae Young Shin, Nae-Gyu Kang, Sanghwa Lee
Summary: This study investigated the antiandrogenic effects of FMN in prostate cancer cells. FMN inhibited androgen receptor protein expression, decreased PSA level, and downregulated androgen regulated genes. FMN bound to androgen receptor and regulated androgen receptor signaling through the PI3K-AktMDM2 pathway.
EUROPEAN JOURNAL OF PHARMACOLOGY
(2022)
Article
Biochemistry & Molecular Biology
Longjun Ma, Yan Zhou, Dehua Yang, Ming-Wei Wang, Wei Lu, Jiyu Jin
Summary: Hydroxymethylthiohydantoin, hydroxymethylthiohydantoin, and hydantoin, all containing a pyridine group, were synthesized to investigate their androgen receptor antagonistic activities. Among them, compounds 6a/6c/7g/19a/19b showed remarkable antagonistic activity against the androgen receptor, comparable to or even surpassing enzalutamide. Additionally, compounds 19a and 19b exhibited superior antiproliferative activity compared to enzalutamide in prostate cancer cells. These findings suggest that compound 19a holds promising potential as a novel AR antagonist.
Article
Food Science & Technology
Jingqi Zhao, Yantong Sun, Li Ren, Shuqing Huang, Jie Zhang
Summary: Aloe-emodin, a novel androgen receptor (AR) antagonist, has been identified to inhibit AR signaling by promoting apoptosis, modulating AR protein levels, inhibiting AR downstream target genes, and preventing the nuclear translocation of AR. These findings suggest that aloe-emodin may play a crucial role in prostate cancer prevention and treatment.
FOOD AND CHEMICAL TOXICOLOGY
(2023)
Article
Biochemistry & Molecular Biology
Qian Xu, Zixiong Zhang, Chenchao Huang, Qiqi Bao, Rongyu Zhang, Meng Wu, Xiaohui Xiao, Xiaoli Han, Xiaoyu Li, Jinming Zhou
Summary: The androgen signaling pathway is crucial in prostate cancer (PCa), and the anti-androgen drug Darolutamide (ODM-201) shows promising activity against the androgen receptor. This study synthesized 37 analogues of ODM-201 with half of them exhibiting similar or better anti-AR transcriptional activity, and compound 28t showed superior inhibitory activity against resistant mutants.
BIOORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yuya Sugiyama, Ryuhei Shirai, Masaki Hirose, Tomoko Watanabe, Ayana Yoshida, Natsuki Endo, Toshiya Hayashi, Takayuki Shioiri, Masato Matsugi
SYNTHESIS-STUTTGART
(2017)
Article
Chemistry, Organic
Yuki Kobayashi, Naoki Suzumura, Yuki Tsuchiya, Machiko Goto, Yuya Sugiyama, Takayuki Shioiri, Masato Matsugi
SYNTHESIS-STUTTGART
(2017)
Article
Chemistry, Organic
Kotaro Ishihara, Mayumi Kawashima, Takatoshi Matsumoto, Takayuki Shioiri, Masato Matsugi
SYNTHESIS-STUTTGART
(2018)
Article
Chemistry, Organic
Kotaro Ishihara, Takayuki Shioiri, Masato Matsugi
TETRAHEDRON LETTERS
(2017)
Article
Chemistry, Organic
Yuki Kobayashi, Rina Igarashi, Yuta Ishikawa, Sae Inukai, Kento Shimowaki, Yuya Sugiyama, Takayuki Shioiri, Masato Matsugi
Article
Chemistry, Organic
Yuki Kobayashi, Riho Obayashi, Yuki Watanabe, Hiroki Miyazaki, Issei Miyata, Yuta Suzuki, Yukihiro Yoshida, Takayuki Shioiri, Masato Matsugi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Kotaro Ishihara, Takayuki Shioiri, Masato Matsugi
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Organic
Kazuki Ishihara, Riho Obayashi, Machiko Gotoh, Yuki Watanabe, Yuki Kobayashi, Kotaro Ishihara, Takayuki Shioiri, Masato Matsugi
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Organic
Kotaro Ishihara, Takayuki Shioiri, Masato Matsugi
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Organic
Kotaro Ishihara, Takayuki Shioiri, Masato Matsugi
Article
Chemistry, Organic
Kotaro Ishihara, Kazuki Ishihara, Yota Tanaka, Takayuki Shioiri, Masato Matsugi
Summary: Tetrazoles can be effectively synthesized using non-toxic or explosive reagents, diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate, in the presence of aromatic bases.
Article
Chemistry, Organic
Kotaro Ishihara, Takayuki Shioiri, Masato Matsugi
Summary: A novel method has been developed for the synthesis of 1,5-disubstituted tetrazoles from nitrones, allowing the preparation of tetrazoles without the need for toxic or explosive reagents.
Article
Chemistry, Organic
Kotaro Ishihara, Takayuki Shioiri, Masato Matsugi
Summary: A novel method using diphenyl phosphorazidate was developed for the synthesis of carbamoyl azides from hydroxamic acids. This method avoids the use of highly explosive reagents and allows the conversion of various hydroxamic acids into the corresponding carbamoyl azides.
TETRAHEDRON LETTERS
(2022)
Review
Chemistry, Organic
Takayuki Shioiri, Kotaro Ishihara, Masato Matsugi
Summary: DPPA has been described as a versatile synthetic reagent that can be used for various chemical reactions, including amide synthesis, ester synthesis, and rearrangement reactions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Kazuki Ishihara, Riho Obayashi, Mizuki Ohira, Yuki Kobayashi, Kotaro Ishihara, Yamato Kato, Narisa Takeuchi, Risa Mizuno, Takayuki Shioiri, Masato Matsugi
Summary: The immobilized fluorous-tagged proline catalyst, with acidic sulfonamide groups bearing multifluorous tags at the carboxy position, proved to be more effective in achieving high stereoselectivity than introducing bulky substituents on the proline backbone. The Teflon (R)-immobilized proline catalyst could be recovered and reused at least five times while maintaining high levels of catalytic activity and stereoselectivity.
