637-04-7Relevant articles and documents
Design, Synthesis, and Antifungal Activity of 2,6-Dimethyl-4-aminopyrimidine Hydrazones as PDHc-E1 Inhibitors with a Novel Binding Mode
Zhou, Yuan,Zhang, Shasha,Cai, Meng,Wang, Kaixing,Feng, Jiangtao,Xie, Dan,Feng, Lingling,Peng, Hao,He, Hongwu
, p. 5804 - 5817 (2021/06/25)
A series of novel 2,6-dimethyl-4-aminopyrimidine hydrazones 5 were rationally designed and synthesized as pyruvate dehydrogenase complex E1 (PDHc-E1) inhibitors. Compounds 5 strongly inhibited Escherichia coli (E. coli) PDHc-E1 (IC50 values 0.94-15.80 μM). As revealed by molecular docking, site-directed mutagenesis, enzymatic, and inhibition kinetic analyses, compounds 5 competitively inhibited PDHc-E1 and bound in a "straight"pattern at the E. coli PDHc-E1 active site, which is a new binding mode. In in vitro antifungal assays, most compounds 5 at 50 μg/mL showed more than 80% inhibition against the mycelial growth of six tested phytopathogenic fungi, including Botrytis cinerea, Monilia fructigena, Colletotrichum gloeosporioides, andBotryosphaeria dothidea. Notably, 5f and 5i were 1.8-380 fold more potent against M. fructigena than the commercial fungicides captan and chlorothalonil. In vivo, 5f and 5i controlled the growth of M. fructigena comparably to the commercial fungicide tebuconazole. Thus, 5f and 5i have potential commercial value for the control of peach brown rot caused by M. fructigena.
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
Bi, Fangchao,Song, Di,Qin, Yinhui,Liu, Xingbang,Teng, Yuetai,Zhang, Na,Zhang, Panpan,Zhang, Nan,Ma, Shutao
, p. 3179 - 3193 (2019/06/17)
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.
Synthesis of Aryl Hydrazines via CuI/BMPO Catalyzed Cross-Coupling of Aryl Halides with Hydrazine Hydrate in Water
Kumar, Siripuram Vijay,Ma, Dawei
supporting information, p. 1003 - 1006 (2018/09/20)
The N,N’-bis(2,6-dimethylphenyl)oxalamide was discovered as a powerful ligand for Cu-catalyzed cross-coupling of aryl halides with hydrazine hydrate, leading to the formation of a variety of aryl hydrazines at 80 oC in water under the assistance of K3PO4 and 4 mol% cetyltrimethylammonium bromide from aryl bromides and aryl iodides. Good to excellent yields were observed in most cases.
Design, synthesis and biological evaluation of glutamic acid derivatives as anti-oxidant and anti-inflammatory agents
Pagire, Suvarna H.,Lee, Eunhye,Pagire, Haushabhau S.,Bae, Eun Jung,Ryu, Soo Jung,Lee, Dahye,Kim, Min Hee,Kim, Geum Ran,Hwang, Kyu-Seok,Ahn, Sukyung,Maeng, Jin Hee,Song, Jin Sook,Bae, Myung Ae,Lee, Don Hang,Ahn, Jin Hee
, p. 529 - 532 (2018/01/04)
A series of glutamic acid derivatives was synthesized and evaluated for their antioxidant activity and stability. We found several potent and stable glutamic acid derivatives. Among them, compound 12b exhibited good in vitro activity, chemical stability and cytotoxicity. A prototype compound 12b showed an anti-inflammatory effect in LPS-stimulated RAW 264.7 cell lines and in a zebrafish model.
Rhodium(III)-catalyzed in situ oxidizing directing group- assisted c-h bond activation and olefination: A route to 2-vinylanilines
Muralirajan, Krishnamoorthy,Haridharan, Radhakrishnan,Prakash, Sekar,Cheng, Chien-Hong
supporting information, p. 761 - 766 (2015/03/18)
A new and efficient method for the synthesis of 2-vinylanilines from the reaction of arylhydrazine hydrochlorides with alkenes and diethyl ketone via a rhodium-catalyzed C-H activation is described. The oxidant-free olefination reaction involves the in situ generation of an -N-N=CR1R2 moiety as the oxidizing directing group thus providing an easy access to 2-vinylanilines.
Synthesis, fungicidal activity, structure-activity relationship and density functional theory studies of novel oxime ether derivatives containing 1-aryl-3-oxypyrazoles
Lv, Kunzhi,Liu, Yuanyuan,Li, Yi,Xu, Guanghui,Pan, Xuechun,Li, Fangshi,Chen, Kai,Huang, Bin,Yang, Yaping
, p. 594 - 600 (2015/11/27)
A series of 16 oxime ether derivatives containing 1-aryl-3-oxypyrazoles were synthesised, and the structure of one of them, (E)-methyl 2-(2-({(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy}methyl)phenyl)-2-(methoxyimino)acetate was determined by X-ray diffraction crystallography. Preliminary bioassays indicated that some of these compounds exhibited very good fungicidal activities against Rhizoctonia solani, especially the ester 2-(2-({(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy}methyl)phenyl)-2-(methoxyimino)acetate, which displayed greater activity than control compound pyraclostrobin at a dosage of 0.1 μg mL-1. The relationship between structure and fungicidal activity was discussed. Density functional theory studies of the 3-methyl heterocyclic ester and the 4-chorophenyl heterocyclic N-methylamide were carried out and the results discussed in terms of the wide difference in fungicidal activity shown by each compound.
Design, synthesis, crystal structures, and insecticidal activities of eight-membered azabridge neonicotinoid analogues
Xu, Renbo,Xia, Rui,Luo, Ming,Xu, Xiaoyong,Cheng, Jiagao,Shao, Xusheng,Li, Zhong
, p. 381 - 390 (2014/02/14)
Three series of novel azabridge neonicotinoid analogues were designed and synthesized, which were constructed by starting material A, glutaraldehyde, and primary amine hydrochlorides (aliphatic amines, phenylhydrazines, and anilines). Most of the eight-membered azabridge compounds presented higher insecticidal activities than oxabridged compound B against cowpea aphid (Aphis craccivora) and brown planthopper (Nilaparvata lugens). Compared with imidacloprid, some azabridged compounds exhibited excellent insecticidal activity against brown planthopper. The crystal structures and bioassay indicated that changing bridge atoms from O to N could lead to entirely different conformations, which might be the important influential factor of the bioactivities.
Regioselective synthesis of indoles via rhodium-catalyzed C-H activation directed by an in-situ generated redox-neutral group
Muralirajan, Krishnamoorthy,Cheng, Chien-Hong
, p. 1571 - 1576 (2014/06/09)
A regioselective synthesis of indoles from arylhydrazine hydrochlorides with alkynes and diethyl ketone catalyzed by a rhodium complex is described. A possible mechanism involving an in-situ generated oxidizing directing group -N-Ni'CR1R2 assisted ortho-C-H activation and reductive elimination are proposed. The catalytic reaction is highly compatible with a wide range of functional arylhydrazines and alkynes. The reaction proceeds under mild reaction conditions and is atom-step economical.
Indole synthesis by rhodium(III)-catalyzed hydrazine-directed C-H activation: Redox-neutral and traceless by N-N bond cleavage
Zhao, Dongbing,Shi, Zhuangzhi,Glorius, Frank
supporting information, p. 12426 - 12429 (2013/12/04)
Fishing for complements! There is an alternative to the useful Fischer indole synthesis. The new method utilizes the same retrosynthetic disconnection but is based on a RhIII-catalyzed directed C-H activation step and a successive coupling with alkynes. Copyright
Synthesis, crystal structure and fungicidal activities of new type oxazolidinone-based strobilurin analogues
Li, Yuhao,Liu, Rui,Yan, Zhangwei,Zhang, Xiangning,Zhu, Hongjun
experimental part, p. 3341 - 3347 (2012/05/05)
A series of oxazolidinone-based strobilurin analogues were efficiently synthesized by the reaction of 3-(2-bromomethylphenyl) oxazolidin-2-one with 1-substituted phenyl-2H-pyrazolin-3-one. Their structures were confirmed and characterized by 1H-NMR, 13C-NMR, elemental analysis, and mass spectroscopy. In addition, the crystal structure of the target compound 3-(2-((1-phenyl-2H-pyrazol-3-yloxy)methyl)phenyl) oxazolidin-2-one was determined by single crystal X-ray diffraction. The bioassay results of these compounds indicated that some of the oxazolidin-2-one derivatives containing N-substituted phenyl 2H-pyrazol ring exhibited potential in vivo fungicidal activities against M. grisea at the dosage of 1 g L-1.
