28284-05-1Relevant articles and documents
Synthesis and biological evaluation of N-naphthoyl-phenylglyoxamide-based small molecular antimicrobial peptide mimics as novel antimicrobial agents and biofilm inhibitors
Nizalapur, Shashidhar,Ho, Kitty K. K.,Kimyon, ?nder,Yee, Eugene,Berry, Thomas,Manefield, Mike,Cranfield, Charles G.,Willcox, Mark,Black, David StC,Kumar, Naresh
, p. 3623 - 3637 (2016)
Antimicrobial peptides (AMPs) are a key component of the human immune system. Synthetic AMP mimics represent a novel strategy to counteract the increasing incidence of antimicrobial resistance. Here, we describe the synthesis of novel glyoxamide derivativ
New hydrazides derivatives of isoniazid against Mycobacterium tuberculosis: Higher potency and lower hepatocytotoxicity
Castelo-Branco, Frederico Silva,de Lima, Evanoel Crizanto,Domingos, Jorge Luiz de Oliveira,Pinto, Angelo C.,Louren?o, Maria Cristina S.,Gomes, Karen Machado,Costa-Lima, Mariana Marques,Araujo-Lima, Carlos Fernando,Aiub, Claudia Alessandra Fortes,Felzenszwalb, Israel,Costa, Thadeu Estevam M.M.,Penido, Carmen,Henriques, Maria G.,Boechat, Nubia
, p. 529 - 540 (2018)
Tuberculosis (TB) is one of the leading causes of death worldwide. The emergence of multi-drug resistant strains of Mycobacterium tuberculosis (Mtb) and TB-HIV co-infection are major public health challenges. The anti-TB drugs of first choice were developed more than 4 decades ago and present several adverse effects, making the treatment of TB even more complicated and the development of new chemotherapeutics for this disease imperative. In this work, we synthesized two series of new acylhydrazides and evaluated their activity against different strains of Mtb. Derivatives of isoniazid (INH) showed important anti-Mtb activity, some being more potent than all anti-TB drugs of first choice. Moreover, three compounds proved to be more potent than INH against resistant Mtb. The Ames test showed favorable results for two of these substances compared to INH, one of which presented expressly lower toxicity to HepG2 cells than that of INH. This result shows that this compound has the potential to overcome one of the main adverse effects of this drug.
Discovery of Isatin-Based Carbohydrazones as Potential Dual Inhibitors of Fatty Acid Amide Hydrolase and Monoacylglycerol Lipase
Jaiswal, Shivani,Ayyannan, Senthil Raja
, (2021/11/09)
Using ligand-based design strategy, a set of isatin-3-carbohydrazones was designed, synthesized and evaluated for dual fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL) inhibition properties. Compound 5-chloro-N′-(5-chloro-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 b) emerged as a potent MAGL inhibitor with nanomolar activity (IC50=3.33 nM), while compound 5-chloro-N′-(1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 j) was the most potent selective FAAH inhibitor (IC50=37 nM). Compound 5-chloro-N′-(6-chloro-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 c) showed dual FAAH-MAGL inhibitory activity with an IC50 of 31 and 29 nM respectively. Enzyme kinetics studies revealed that the isatin-based carbohydrazones are reversible inhibitors for both FAAH and MAGL. Further, blood-brain permeability assay confirmed that the lead compounds (13 b, 13 c, 13 g, 13 m and 13 q) are suitable as CNS candidates. Molecular dynamics simulation studies revealed the putative binding modes and key interactions of lead inhibitors within the enzyme active sites. The lead dual FAAH-MAGL inhibitor 13 c showed significant antioxidant activity and neuroprotection in the cell-based cytotoxicity assay. In summary, the study yielded three potent FAAH/MAGL inhibitor compounds (13 b, 13 c and 13 j) with acceptable pharmacokinetic profile and thus can be considered as promising candidates for treating neurological and mood disorders.
BIOMASS DERIVED DIKETONES AS EFFICIENT VISIBLE LIGHT PHOTOINITIATORS
-
Paragraph 00192; 00210-00213, (2021/11/26)
Isatin derivatives, and methods of using isatin and isatin derivatives as photoinitiators, are described.
Synthesis of some N-aroyl-2-oxindole benzenesulfonamide conjugates with carbonic anhydrase inhibitory activity
Awadallah, Fadi M.,Bua, Silvia,George, Riham F.,Supuran, Claudiu T.
, (2020/02/06)
Implication of carbonic anhydrases (CAs) in many physiological functions made them attractive therapeutic targets. Herein, we report the synthesis of three series of benzenesulfonamide-based compounds (5a-e, 9a-e and 10a-e) as potential ligands to four of
Selective C?N Bond Cleavage of N-Acylisatins: Towards High Performance Acylation/Arylation/Transamination Reagents
Xiong, Li,Deng, Rong,Liu, Tingting,Luo, Zhongfeng,Wang, Zijia,Zhu, Xiao-Feng,Wang, Hui,Zeng, Zhuo
supporting information, p. 5383 - 5391 (2019/11/03)
New multipurpose arylation/acylation/transamination reagents, N-acylisatins, have been developed by selective ‘inside-outside’ C?N bond cleavage under different catalytic conditions. As activated amides, N-acylisatins undergo Rh-catalyzed C?H arylation and Pd-catalyzed acylation by cleavage outside the C?N bond, and the desired biaryls and diaryl ketones were obtained in good to excellent yields. Generally, the combination of N-acylisatins with amines leads to a ring-opening reaction and formation of transamination products in a predictable manner through inside C?N bond cleavage. Interestingly, treatment of N-acylisatins with amines lead to unexpected outer-ring transamination products when CsF is added, which shows that CsF can favor the outside C?N bond cleavage path. Notably, this work presents a new strategy for multiple chemical transformations of a single amide to achieve various products by selective C?N bond cleavage. (Figure presented.).
a-KETOACYLIC ISONIAZID COMPOUNDS, PROCESS FOR PRODUCING SAID COMPOUNDS, USE OF THE COMPOUNDS IN THE TREATMENT OF TUBERCULOSIS
-
Paragraph 0050-0055, (2018/02/03)
The instant invention relates to compounds of formula I wherein: R is selected from H, Me or Cl, and R′ is selected from: H, NH2, NHCOCH3 NHCOCF3 or NHCOCH2Cl. The invention further provides a process for obtaining the compounds of formula I and their use.
Silver-Mediated Synthesis of 4H-Benzoxazin-4-ones by Intramolecular Decarboxylative O-Acylation Reactions with α-Oxocarboxylic Acid
Bharathimohan, Kuppusamy,Ponpandian, Thanasekaran,Jafar, Ahamed A.
, p. 2806 - 2813 (2017/05/29)
The first example of an intramolecular decarboxylative acylation reaction for the synthesis of 4H-benzoxazin-4-one derivatives has been described. The silver-mediated reaction has a broad substrate scope and provides a mild and rapid approach to the corre
N-aroylated isatins: Antiglycation activity
Khan, Khalid Mohammed,Mughal, Uzma Rasool,Khan, Ambreen,Naz, Farzana,Perveen, Shahnaz,Choudhary, M. Iqbal
experimental part, p. 188 - 193 (2011/02/21)
A series of N-aroylated isatins 1-15 was synthesized and evaluated for their antiglycation activity. All compounds showed a varying degree of glycation inhibitory activity with IC50 values between 18.01 ± 0.05-693.7 ± 3.0 μM, when compared with the standard (aminoguanidine) having an IC50 = 268.7 ± 12.4 μM. Compound 1 was found to be the most active member of this series with an IC50 = 18.01 ± 0.05 μM. Compound 10 showed an IC50 = 72.5 ± 0.09 μM, whereas compound 7 has an IC50 = 80.18 ± 0.07 μM. Compounds 3, 9, and 13 showed IC50 values 170.2 ± 0.62, 117.91 ± 2.9, 171.3 ± 0.79 μM, respectively. Rest of the compounds along with parent isatin were found to be inactive. The structures of all the synthetic compounds were deduced by spectroscopic analysis.
Hydrogen bonding in glyoxylamides
Black, David StC.,Condie, Glenn C.,Craig, Donald C.,McConnell, Darryl B.
, p. 141 - 146 (2007/10/03)
A range of secondary 2-amidophenylglyoxylamides self-assemble by intermolecular hydrogen bonding between the secondary amide proton and the 2-amidophenyl carbonyl oxygen atom.
