40019-44-1Relevant articles and documents
Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine
Wu, Weiping,Fan, Shuaixin,Li, Tielei,Fang, Lili,Chu, Benfa,Zhu, Jin
supporting information, p. 5652 - 5657 (2021/08/01)
Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.
Synergism of a novel 1,2,4-oxadiazole-containing derivative with oxacillin against methicillin-resistant staphylococcus aureus
Buommino, Elisabetta,D’auria, Maria Valeria,De Marino, Simona,Festa, Carmen,Piccolo, Marialuisa,Sciarretta, Martina
, (2021/11/01)
Staphylococcus aureus is an important opportunistic pathogen that causes many infections in humans and animals. The inappropriate use of antibiotics has favored the diffusion of methicillin-resistant S. aureus (MRSA), nullifying the efforts undertaken in
SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)
Ding, Chengrong,Ge, Shuting,Wei, Junjie,Zhang, Guofu,Zhao, Yiyong
, p. 17288 - 17292 (2020/05/18)
A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.
Novel phthalide derivatives: Synthesis and anti-inflammatory activity in vitro and in vivo
Chen, Liu Zeng,Wu, Jing,Li, Kang,Wu, Qian Qian,Chen, Rui,Liu, Xin Hua,Ruan, Ban Feng
, (2020/08/21)
Phthalide is a promising chemical scaffold and has been proved to show potent anti-inflammatory efficacy. In this study, three series, total of 31 novel phthalide derivatives were designed and synthesized, their anti-inflammatory activities were screened
Investigation around the Oxadiazole Core in the Discovery of a New Chemotype of Potent and Selective FXR Antagonists
Festa, Carmen,Finamore, Claudia,Marchianò, Silvia,Di Leva, Francesco Saverio,Carino, Adriana,Monti, Maria Chiara,Del Gaudio, Federica,Ceccacci, Sara,Limongelli, Vittorio,Zampella, Angela,Fiorucci, Stefano,De Marino, Simona
supporting information, p. 504 - 510 (2019/01/26)
Recent findings have shown that Farnesoid X Receptor (FXR) antagonists might be useful in the treatment of cholestasis and related metabolic disorders. In this paper, we report the discovery of a new chemotype of FXR antagonists featured by a 3,5-disubsti
A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement
Zhang, Guofu,Zhao, Yiyong,Ding, Chengrong
supporting information, p. 7684 - 7688 (2019/08/30)
A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.
Structure-activity and structure-property relationships of novel Nrf2 activators with a 1,2,4-oxadiazole core and their therapeutic effects on acetaminophen (APAP)-induced acute liver injury
Xu, Li-Li,Wu, Yu-Feng,Wang, Lei,Li, Cui-Cui,Li, Li,Di, Bin,You, Qi-Dong,Jiang, Zheng-Yu
, p. 1376 - 1394 (2018/09/13)
The antioxidant function induced by Nrf2 protects the liver from damage. We found a novel Nrf2 activator named compound 25 via structural modification of compound 1 we previously reported. In vitro, compound 25 induced Nrf2 transport into the nucleus and protected hepatocyte L02 cells from APAP-induced cytotoxicity via activating the Nrf2-ARE signaling pathway. In vivo, 25 exhibited therapeutic effects in a mouse model of acute liver injury induced by acetaminophen (APAP) by up-regulating Nrf2-dependent antioxidases and down-regulating liver injury markers in serum. Together, these results indicated that 25 is a potent Nrf2/ARE activator both in vitro and in vivo. The drug-like properties of compound 25 further revealed its potential for development as a therapeutic drug against acute liver injury.
One-pot synthesis of highly substituted polyheteroaromatic compounds by rhodium(III)-catalyzed multiple C-H activation and annulation
Jayakumar, Jayachandran,Parthasarathy, Kanniyappan,Chen, Yi-Hsiang,Cheng, Chien-Hong,Lee, Tai-Hua,Chuang, Shih-Ching
supporting information, p. 9889 - 9892,4 (2014/11/08)
A new method for the synthesis of highly substituted naphthyridine-based polyheteroaromatic compounds in high yields proceeds through rhodium(III)-catalyzed multiple C-H bond cleavage and C-C and C-N bond formation in a one-pot process. Such highly substituted polyheteroaromatic compounds have attracted much attention because of their unique π-conjugation, which make them suitable materials for organic semiconductors and luminescent materials. Furthermore, a possible mechanism, which involves multiple chelation-assisted ortho C-H activation, alkyne insertion, and reductive elimination, is proposed for this transformation.
Synthesis and cannabinoid activity of 1-substituted-indole-3-oxadiazole derivatives: Novel agonists for the CB1 receptor
Moloney, Gerard P.,Angus, James A.,Robertson, Alan D.,Stoermer, Martin J.,Robinson, Michael,Wright, Christine E.,McRae, Ken,Christopoulos, Arthur
, p. 513 - 539 (2008/12/21)
An exploratory chemical effort has been undertaken to develop a novel series of compounds as selective CB1 agonists. It is hoped that compounds of this type will have clinical utility in pain control, and cerebral ischaemia following stroke or traumatic head injury. We report here medicinal chemistry studies directed towards the investigation of a series of 1-substituted-indole-3-oxadiazoles as potential CB1 agonists. Crown Copyright
New oxadiazole derivatives showing partly antiplatelet, antithrombotic and serotonin antagonistic properties
Bethge, Katrin,Pertz, Heinz H.,Rehse, Klaus
, p. 78 - 86 (2007/10/03)
Ten new 1,2,4-oxadiazole- and six new 1,3,4-oxadiazole-carboxamides containing different lipophilic moieties (i.e. 4-biphenyl-, 1-naphthyl, phenylpropyl- and n-hexyl substituents) and additional basic groups which are mainly alkyl- and dialkylaminoalkyl residues have been synthesized and tested for antiplatelet effects in vitro (Born-test) and antithrombotic properties in vivo (laser thrombosis model). If the platelet aggregation was induced by collagen, the inhibitory effects (IC50) were between 58 μM and 300 μM. Using serotonin (5-HT) as an inducer, compound 6a (N-(3-dimethylaminopropyl-5- (biphenyl-4-yl)-1,3,4-oxadiazole-2-carboxamide) had an IC50 = 1 μM (12e: (N-3-Dimethylaminopropyl)-3-(1-naphthyl)-1,2,4-oxadiazole-5-carboxamide, 6.7 μM). In an in vitro rat tail artery assay 6a and 12e behaved as a competitive 5-HT2A receptor antagonist (6a: pKB = 6.86 ± 0.04; 12e: pKB = 6.66 ± 0.05). The antithrombotic effects of some compounds were small but significant (7-10% inhibition of thrombus formation).
