- Investigation of Masked N-Acyl-N-isocyanates: Support for Oxadiazolones as Blocked N-Isocyanate Precursors
-
In contrast to carbon-substituted isocyanates that are common building blocks, N-substituted isocyanates remain underdeveloped and reports on their N-acyl derivatives (i. e. amido-isocyanates) are exceedingly rare. Herein, amido-isocyanates were investiga
- Gagné-Monfette, William,Vincent-Rocan, Jean-Fran?ois,Lutes, Owen C.,O'Keefe, Geneviève F.,Jeanneret, Alexandria D. M.,Blanger, Claire,Ivanovich, Ryan A.,Beauchemin, André M.
-
supporting information
p. 14051 - 14056
(2021/09/14)
-
- Discovery of 1,3,4-oxadiazol-2-one-containing benzamide derivatives targeting FtsZ as highly potent agents of killing a variety of MDR bacteria strains
-
The spread of infections caused by multidrug-resistant (MDR) pathogens, such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant S. aureus (VRSA), has created a need for new antibiotics with novel mechanisms of action. The bacterial division protein FtsZ has been identified as a novel drug target that can be exploited clinically. As part of an ongoing effort to develop FtsZ-targeting antibacterial agents, we describe herein the design, synthesis and bioactivity of six series of novel 1,3,4-oxadiazol-2-one-containing, 1,2,4-triazol-3-one-containing and pyrazolin-5-one-containing benzamide derivatives. Among them, compound A14 was found to be the most potent antibacterial agent, much better than clinical drugs such as ciprofloxacin, linezolid and erythromycin against all the tested gram-positive strains, particularly methicillin-resistant, penicillin-resistant and clinical isolated S. aureus. Subsequent studies on biological activities and docking analyses proved that A14 functioned as an effective compound targeting FtsZ. Preliminary SAR indicated a general direction for further optimization of these novel analogues. Taken together, this research provides a promising chemotype for developing newer FtsZ-targeting bactericidal agents.
- Bi, Fangchao,Song, Di,Qin, Yinhui,Liu, Xingbang,Teng, Yuetai,Zhang, Na,Zhang, Panpan,Zhang, Nan,Ma, Shutao
-
p. 3179 - 3193
(2019/06/17)
-
- DMF as Methine Source: Copper-Catalyzed Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles
-
An unprecedented Cu-catalyzed direct annulation of hydrazides with N,N-dimethylformamide (DMF) was developed, providing an efficient synthesis of valuable 1,3,4-oxadiazoles. This process features the short reaction time and can be safely conducted on gram scale. The reaction also facilitated the convenient synthesis of 1,3,4-oxadiazole-2(3H)-ones. Moreover, the mechanistic studies suggest that the source of CH is from the N-methyl group of DMF. (Figure presented.).
- Wang, Shoucai,Wang, Kai,Kong, Xiangfei,Zhang, Shuhua,Jiang, Guangbin,Ji, Fanghua
-
supporting information
p. 3986 - 3990
(2019/07/31)
-
- Synthesis and In Vitro Anticancer Activity of Novel 1,3,4-Oxadiazole-Linked 1,2,3-Triazole/Isoxazole Hybrids
-
A series of new 1,3,4-oxadiazole-linked 1,2,3-triazole/isoxazole derivatives were designed and synthesized. All the synthesized compounds were screened for in vitro anticancer activity against four human cancer cells: HeLa (cervical), MDA-MB-231 (breast), DU-145 (prostate), and HEPG2 (liver). Among 17 compounds tested, 7a, 7c, and 7d showed potent activity toward four cell lines.
- Madhavilatha,Bhattacharjee, Debanjan,Sabitha, Gowravaram,Reddy, B. V. Subba,Yadav,Jain, Nishant,Reddy, B. Jagan Mohan
-
p. 863 - 870
(2018/02/12)
-
- Palladium-catalyzed oxidative O-H/N-H carbonylation of hydrazides: Access to substituted 1,3,4-oxadiazole-2(3 H)-ones
-
A novel palladium-catalyzed oxidative annulation reaction for the C-O, C-N bond formations is developed. The intramolecular cyclocarbonylation provides an efficient and direct approach for the construction of valuable 1,3,4-oxadiazole-2(3H)-ones and their
- Ji, Fanghua,Li, Xianwei,Guo, Wei,Wu, Wanqing,Jiang, Huanfeng
-
p. 5713 - 5718
(2015/06/16)
-
- Synthesis of 5-substituted-3H-[1,3,4]-oxadiazol-2-one derivatives: A carbon dioxide route (CDR)
-
A carbon dioxide route (CDR) for making biologically important 5-substituted-3H-[1,3,4]-oxadiazol-2-ones (SHOs) has been accomplished through synthesis and cyclization of a variety of hydrazides as the key intermediates. All of these hydrazides were prepared readily in 89-97% yields by reacting acid chlorides with a hydrazine monohydrate in the initial step. Then, SHOs were obtained in high yields from hydrazides by reacting them with carbon dioxide under basic conditions. More notable than the high yields, is that the present CDR process for the first time has succeeded in providing a straightforward cyclization reaction leading to SHO formation with simple reagents in ethanol solution.
- Brahmayya,Dai, Shenghong A.,Suen
-
p. 65351 - 65357
(2015/08/18)
-
- Synthesis of 5-aryl-3H-[1,3,4]oxadiazol-2-ones from N′-(chloro-aryl- methylene)-tert-butylcarbazates using basic alumina as an efficient and recyclable surface under solvent-free condition
-
The synthesis of biologically important 5-aryl-3H-[1,3,4]oxadiazol-2-ones has been carried out by heating the easily synthesized N′-(chloro-aryl- methylene)-tert-butylcarbazates on basic alumina surface under solvent-free condition. The dual characteristic of basic alumina as a solid support as well as a nucleophile is successfully exploited in these reactions. The method provides special attributions such as reduced reaction times, easier work-up procedures, and good to excellent yields as well as increased purity of products and most importantly environmentally friendly protocols. The basic alumina is easily recovered and utilized for further reactions several times without serious loss of activity.
- Debnath, Kamalesh,Pathak, Sudipta,Pramanik, Animesh
-
p. 896 - 899
(2013/02/25)
-
- Room-temperature copper-catalyzed oxidation of electron-deficient arenes and heteroarenes using air
-
No pressure: The oxidation of aromatic C-H bonds at room temperature was realized through a copper-catalyzed "oxygenase-type" oxidation of arenes and heteroarenes in the presence of air (see scheme). The reaction involves an oxygen-atom transfer from O2 in the air onto the substrates. Copyright
- Liu, Qiang,Wu, Pan,Yang, Yuhong,Zeng, Ziqi,Liu, Jie,Yi, Hong,Lei, Aiwen
-
p. 4666 - 4670
(2012/06/30)
-
- Some 1-Aroyl-4,4-dialkylsemicarbazides and Their Cyclization to Afford 5-Aryl-1,3,4-oxadiazol-2(3H)-ones
-
Some 1-aroyl-4,4-dialkylsemicarbazides have been prepared by reacting aroyl-hydrazides with dimethyl- or diethyl-carbamoyl chloride.In boiling DMF they lose dimethylamine or diethylamine to give 5-aryl-1,3,4-oxadiazol-2(3H)-ones. - Keywords: 1-Aroyl-4,4-d
- Davidson, John S.
-
p. 1027 - 1030
(2007/10/02)
-
- Synthesis of Substituted N-(2,4-Dioxo-1,2,3,4-tetrahydroquinazolinyl)benzamides and N-(2-Thiono-4-oxo-1,2,3,4-tetrahydroquinazolinyl)benzamides
-
Substuted N-(2,3-dioxo-1,2,3,4-tetrahydroquinazolinyl)benzamides (3a-g) and substituted N-(2-thiono-4-oxo-1,2,3,4-tetrahydroquinazolinyl)benzamides (4a-g) were synthetized in one step from the reaction of methyl anthranilate with 2-aryl-1,3,4-oxadiazolin-5-ones (1a-g) and 2-aryl-1,3,4-oxadiazoline-5-thiones (2a-g), respectively, in m-cresol at 150-160 deg C.Alternative routes leading to the formation of 3a and 4a are also reported.
- Chau, Nguyen,Saegusa, Yasuo,Iwakura, Yoshio
-
p. 541 - 544
(2007/10/02)
-