Organic & Biomolecular Chemistry最新文献_第5页

A review on benzoselenazoles: synthetic methodologies and potential biological applications

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-03-26 DOI: 10.1039/D4OB01897D

Manisha Yadav and Vijay P. Singh

{"title":"A review on benzoselenazoles: synthetic methodologies and potential biological applications","authors":"Manisha Yadav and Vijay P. Singh","doi":"10.1039/D4OB01897D","DOIUrl":"10.1039/D4OB01897D","url":null,"abstract":"Among the various heterocyclic organoselenium compounds, a new class of benzoselenazoles has received great attention due to their chemical properties and biological applications. The ever-growing interest in the five-membered benzoselenazole heterocycles amongst chemists has made commendable impact. These heterocycles are a prominent class of organic molecules that have emerged as potential therapeutic agents for the treatment of a wide range of diseases. Substantial progress has been made in elucidating the complex chemical properties of these heterocycles. Moreover, they have garnered significant importance in a wide range of biological applications. However, despite their biological activities, research on benzoselenazoles remains relatively limited, emphasising the need for further exploration in this area. Hence, considering the importance of benzoselenazoles, this comprehensive review compiles various synthetic procedures, highlighting the recent advances in their synthesis that have been disclosed in the literature. This review would offer chemists an array of information that will assist them in the development of more affordable and effective synthesis processes for benzoselenazoles. Therefore, it is believed that this review would provide relevant context on these achievements and will inspire synthetic organic chemists to use these effective technologies of such heterocycles for the future treatment of diseases caused by oxidative stress. The biological and pharmacological properties of these organoselenium heterocycles, which include their antioxidant, antitumor, and antibacterial activities and their application in Alzheimer's disease treatment and as pancreatic lipase inhibitors, are thoroughly summarized. Finally, this review provides some perspectives on the challenges and future directions in the development of benzoselenazoles as heterocyclic organoselenium compounds.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 16","pages":" 3712-3740"},"PeriodicalIF":2.9,"publicationDate":"2025-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143727234","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Rh(iii)-catalyzed C–H alkenylation of NH-sulfoximine with vinylsilanes†

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-03-25 DOI: 10.1039/D5OB00213C

Yu Gao, Ya-Li Xu and Lin Dong

引用次数: 0

Access to chiral phthalidyl ester prodrugs via an isothiourea-catalyzed dynamic kinetic resolution reaction†

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-03-25 DOI: 10.1039/D4OB02057J

Hui Cai, Chaoyang Song, Dan Ling, Youlin Deng, Zhichao Jin and Tingting Li

引用次数: 0

A novel strategy for alkylation via amide activation: synthesis of N-substituted 2-pyridones and tetrahydropyridines†

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-03-25 DOI: 10.1039/D5OB00140D

Qiao Song, Shun Wang, Sheng Wang, Dong Xing and Zhouyu Wang

引用次数: 0

O-Acylation triggered γ-umpolung functionalization of electron-poor alkenyl sulfoxides for the synthesis of 3-allyl indoles†

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-03-25 DOI: 10.1039/D5OB00112A

Wenjie Wei, Qiangrong Xie, Xiaoyu Li, Yuanyuan Xie and Hongwei Zhou

引用次数: 0

Catalyst and transition-metal free 1,6-conjugate addition of azobisisobutyronitrile: access to isobutyronitrile containing diarylmethanes†

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-03-25 DOI: 10.1039/D5OB00012B

Ajay G. Mamale, Balaji M. Ghodake, Rajesh G. Gonnade and Asish K. Bhattacharya

引用次数: 0

Total synthesis of the HDAC inhibitor (+)-(R)-trichostatin A via O-directed dialkylacetylene free radical hydrostannation with Ph₃SnH/Et₃B. The unusual inhibitory effect of a proximal α-OPv group on the course of a vinyl iodide Stille cross-coupling.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-03-24 DOI: 10.1039/d4ob01848f

Ke Pan, Soraya Manaviazar, Karl J Hale

{"title":"Total synthesis of the HDAC inhibitor (+)-(R)-trichostatin A via O-directed dialkylacetylene free radical hydrostannation with Ph3SnH/Et3B. The unusual inhibitory effect of a proximal α-OPv group on the course of a vinyl iodide Stille cross-coupling.","authors":"Ke Pan, Soraya Manaviazar, Karl J Hale","doi":"10.1039/d4ob01848f","DOIUrl":"10.1039/d4ob01848f","url":null,"abstract":"In this paper, a new asymmetric total synthesis of optically pure (+)-trichostatin A (1a) is described via a route that utilises a Marshall chiral allenylzinc addition between 9 and 4-dimethylaminobenzaldehyde (10) and an O-depivaloylation at its early stages. O-Directed free radical hydrostannation of the resulting propargylic alcohol 15 with Ph3SnH/cat. Et3B/O2 in PhMe at rt thereafter provided the (Z)-α-triphenylstannylvinyltin 16 in 80-89% yield, with complete stereocontrol and very high α : β regioselectivity (25 : 1). A stereoretentive I-Sn exchange reaction between 16 and I2 (1.4 equiv.) in CH2Cl2 (-78 °C to rt, 1 h) subsequently secured the vinyl iodide 18 in 84-96% yield. The latter was transformed into the enal 4 by successive TPAP/NMO (Ley-Griffith) oxidation and a high yielding (80%) Stille reaction between the α-iodo enal 20 and Me4Sn, catalysed by Pd(PPh3)4 in DMF at 60 °C, under the Baldwin-Lee conditions, which use CsF and CuI as promoters. A Wittig reaction between 4 and Ph3PCHCO2Et (5), saponification, and DDQ oxidation next afforded (+)-trichostatic acid (22). Helquist's ethyl chloroformate mixed-anhydride/TBSONH2 coupling procedure (ref. 17e) thereafter secured (+)-trichostatin A (1a) in good yield. This new total synthesis of 1a is the first-ever successful application of the O-directed dialkylacetylene free radical hydrostannation with Ph3SnH/cat. Et3B/O2 in a dialkylaniline N-containing disubstituted alkynol system, and it now provides a convenient means of accessing many novel trichostatin analogues for future biological screening.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143690474","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Effect of hydroxy groups on X-ray-induced reactions of azo benzene derivatives†

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-03-21 DOI: 10.1039/D5OB00003C

Koki Ogawara, Naoya Ieda, Hideo Takakura, Kohei Nakajima, Akari Mukaimine, Mei Harada, Kazuaki Hashimoto, Osamu Inanami and Mikako Ogawa

{"title":"Effect of hydroxy groups on X-ray-induced reactions of azo benzene derivatives†","authors":"Koki Ogawara, Naoya Ieda, Hideo Takakura, Kohei Nakajima, Akari Mukaimine, Mei Harada, Kazuaki Hashimoto, Osamu Inanami and Mikako Ogawa","doi":"10.1039/D5OB00003C","DOIUrl":"10.1039/D5OB00003C","url":null,"abstract":"Caged compounds whose chemical bonds are cleavable by specific stimuli are useful tools for life science research because they facilitate control of various biological activities spatiotemporally. Although caged compounds activatable by hard X-rays can be employed for control in deep tissue owing to the high bio-permeability of X-rays, chemical bond cleavage by ionizing radiation has not been investigated adequately. Previously, we demonstrated that an azo bond tethered to a rhodamine scaffold can be efficiently cleaved by hydrated electrons, which is one of the radiolysis products of water, to release rhodamine. In this study, we synthesized novel azo benzene derivatives, AZO1–4, which can release 3-aminobenzamide (3-ABA), a poly (ADP-ribose) polymerase (PARP) inhibitor, and hydroxy groups or amino groups were introduced into them in order to assess the substituent effect on azo bond cleavage. While the amount of 3-ABA was nearly the same for all the azo compounds, decomposition of azo compounds increased according to the number of hydroxy groups. Furthermore, a methoxyl-radical-adding product was detected from AZO2. These results suggested that the hydroxy group accelerates not azo bond cleavage but the other decomposition pathway.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 15","pages":" 3595-3600"},"PeriodicalIF":2.9,"publicationDate":"2025-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/ob/d5ob00003c?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143672952","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Solvatomorphism of a 2,6-pyridyldicarboxamide-based foldamer.

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-03-21 DOI: 10.1039/d5ob00342c

Sena Ozturk, Alexander R Davis, Colin C Seaton, Louise Male, Sarah J Pike

{"title":"Solvatomorphism of a 2,6-pyridyldicarboxamide-based foldamer.","authors":"Sena Ozturk, Alexander R Davis, Colin C Seaton, Louise Male, Sarah J Pike","doi":"10.1039/d5ob00342c","DOIUrl":"https://doi.org/10.1039/d5ob00342c","url":null,"abstract":"A detailed solvatomorphism study conducted on a diamine-terminated 2,6-pyridyldicarboxamide-based foldamer 1 is reported. This investigation establishes the influence of a diverse range of polar and non-polar solvents including chloroform (1A), a trifluorotoluene/dichloromethane mixture (1A), dimethylformamide/diethyl ether (1B), tetrahydrofuran (1·THF), butanone (1·butanone), dichloromethane (1·DCM), a methanol/dichloromethane mixture (1·MeOH) and dimethylsulfoxide (1·DMSO) on the solid-state conformation and crystal packing behaviour of this supramolecular scaffold. Single-crystal X-ray diffraction analysis of the seven solvatomorphs of the studied foldamer (1A, 1B, 1·DCM, 1·THF, 1·butanone, 1·MeOH and 1·DMSO) identified that 1·DCM, 1·THF, 1·butanone, 1·MeOH and 1·DMSO form supramolecular aggregates (e.g., channels/cavities) which incorporate solvent molecules within the voids of the system, leading them to adopt channels of differing dimensions between 3.5 and 9.0 Å. Solid-state analysis identified that a diverse array of intermolecular non-covalent interactions form between the foldamer and the solvent molecule, including N-H⋯O, N-H⋯Cl, O-H⋯O, N-H⋯Cl and C-H⋯O hydrogen-bonding interactions, stabilising the formation of these solvent-mediated channel aggregates within the different solvatomorphs of the studied foldamer. We envisage that these solvatomorphism studies will facilitate the future design of foldamers, particularly given the emerging solid-state applications of foldamers which could hold relevance in the field of crystal engineering or for the uptake of small molecules for long-term use in energy storage and materials chemistry.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143668531","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis of 3,4-unsubstituted isoquinolone derivatives from benzimidates and vinylene carbonate via cobalt(iii)-catalyzed C–H activation/cyclization†

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2025-03-20 DOI: 10.1039/D5OB00319A

Weiyan Xu, Haowen Dang, Huiru Sheng, Jiabin Shen and Min Wang

引用次数: 0