37394-93-7Relevant academic research and scientific papers
Synthesis and Anti-Arrhythmic Activity of the Chloride and Salicylate Salts of Morpholinoacetic Acid Ortho-Toluidide
Gashkova,Rudakova,Syropyatov, B. Ya.
, p. 641 - 643 (2017)
Acylation of ortho-toluidine hydrochloride by chloroacetylchloride followed by amination by morpholine in the presence of an excess of Et3N produced morpholinoacetic acid ortho-toluidide and its salicylate salt. The acute toxicity and anti-arrh
Synthesis and Biological Evaluation of Dithiobisacetamides as Novel Urease Inhibitors
Liu, Mei-Ling,Li, Wei-Yi,Fang, Hai-Lian,Ye, Ya-Xi,Li, Su-Ya,Song, Wan-Qing,Xiao, Zhu-Ping,Ouyang, Hui,Zhu, Hai-Liang
, (2021/11/13)
Thirty-eight disulfides containing N-arylacetamide were designed and synthesized in an effort to develop novel urease inhibitors. Biological evaluation revealed that some of the synthetic compounds exhibited strong inhibitory potency against both cell-free urease and urease in intact cell with low cytotoxicity to mammalian cells even at concentration up to 250 μM. Of note, 2,2′-dithiobis(N-(2-fluorophenyl)acetamide) (d7), 2,2′-dithiobis(N-(3,5-difluorophenyl)acetamide) (d24), and 2,2′-dithiobis(N-(3-fluorophenyl)acetamide) (d8) were here identified as the most active inhibitors with IC50 of 0.074, 0.44, and 0.81 μM, showing 32- to 355-fold higher potency than the positive control acetohydroxamic acid. These disulfides were confirmed to bind urease without covalent modification of the cysteine residue and to inhibit urease reversibly with a mixed inhibition mechanism. They also showed very good anti-Helicobacter pylori activities with d8 showing a comparable potency to the clinical used drug amoxicillin. The impressive in vitro biological profile indicated their immense potential as therapeutic agents to tackle H. pylori caused infections.
N-Aryl mercaptoacetamides as potential multi-target inhibitors of metallo-β-lactamases (MBLs) and the virulence factor LasB fromPseudomonas aeruginosa
Brunst, Steffen,Ducho, Christian,Frank, Denia,Hirsch, Anna K. H.,Kramer, Jan S.,Proschak, Ewgenij,Rotter, Marco,Voos, Katrin,Weizel, Lilia,Wichelhaus, Thomas A.,Yahiaoui, Samir,Haupenthal, J?rg
supporting information, p. 1698 - 1708 (2021/11/23)
Increasing antimicrobial resistance is evolving to be one of the major threats to public health. To reduce the selection pressure and thus to avoid a fast development of resistance, novel approaches aim to target bacterial virulence instead of growth. Another strategy is to restore the activity of antibiotics already in clinical use. This can be achieved by the inhibition of resistance factors such as metallo-β-lactamases (MBLs). Since MBLs can cleave almost all β-lactam antibiotics, including the “last resort” carbapenems, their inhibition is of utmost importance. Here, we report on the synthesis andin vitroevaluation ofN-aryl mercaptoacetamides as inhibitors of both clinically relevant MBLs and the virulence factor LasB fromPseudomonas aeruginosa. All testedN-aryl mercaptoacetamides showed low micromolar to submicromolar activities on the tested enzymes IMP-7, NDM-1 and VIM-1. The two most promising compounds were further examined in NDM-1 expressingKlebsiella pneumoniaeisolates, where they restored the full activity of imipenem. Together with their LasB-inhibitory activity in the micromolar range, this class of compounds can now serve as a starting point for a multi-target inhibitor approach against both bacterial resistance and virulence, which is unprecedented in antibacterial drug discovery.
Synthesis of novel 1,2,3-triazoles bearing 2,4 thiazolidinediones conjugates and their biological evaluation
Kulkarni, Pravin S.,Karale, Sanjay N.,Khandebharad, Amol U.,Agrawal, Brijmohan R.,Sarda, Swapnil R.
, p. 2035 - 2046 (2021/02/05)
Searching for new active molecules against M. Bovis BCG and Mycobacterium tuberculosis (MTB) H37Ra, a focused of 1,2,3-triazoles-incorporated 2,4 thiazolidinedione conjugates have been efficiently prepared via a click chemistry approach cyclocondensation of 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide (4), aryl aldehyde (5a–l), and mercapto acetic acid (6) with good to promising yields. The newly synthesized compounds were tested against drug-sensitive MTB and BCG. In particular, compounds 8g, 8h, 8j and 8l are highly potent against both the strains with IC90 values in the range of 1.20–2.70 and 1.24–2.65?μg/mL, respectively. Based on the results from the antitubercular activity, SAR for the synthesized series has been developed. Most of the active compounds were non-cytotoxic against MCF-7, HCT 116 and A549 cell lines. Most active compounds were having a higher selectively index, which suggested that these compounds were highly potent.
Synthesis of (2-chloroquinolin-3-yl)-1,3,4-thiadiazole-2-carboxamides
Aksenov, A. N.,Krayushkin, M. M.,Yarovenko, V. N.
, p. 1131 - 1134 (2021/07/21)
(2-Chloroquinolin-3-yl)-1,3,4-thiadiazole-2-carboxamides were synthesized from hydrazones obtained via the reaction of 3-formyl-2-chloroquinoline with oxamic acid thiohydrazides.
Synthesis, Characterization and Thermal Study of some new Organochalcogenide compounds containing arylamide group
Hassan,Abdulwahid,Al-Luaibi,Al-Jadaan
, p. 5009 - 5015 (2021/08/31)
Two Series of organochalcogen compounds were prepared. The first series was prepared by the reaction of 2-chloro-N-arylacetamide (where aryl is benzyl, phenyl, o-toluene, or p-toluene) with sodium hydrogen selenide (prepared in situ) to give diorganyl selenide compounds (R2Se). The second series was prepared by reaction of N-benzyl-2-chloro-N-(2-chloroacetyl) acetamide with sodium chalcogenate, Na2E (where E= S, Se, and Te) to give the corresponding cyclic chalcogenide compounds. Diiodo derivatives of cyclic selenide and telluride were also prepared. The thermal stability of the new selenium compounds (R2Se) were decomposed at 300°C. Thermogram showed a phase transfer point between 120-150°C indicating that these compounds may act as liquid crystal compounds. All new compounds were characterized by CHN elemental analysis, UV-Visible, FT-IR and 1H NMR spectroscopic data.
A copper-catalyzed synthesis of aryloxy-tethered symmetrical 1,2,3-triazoles as potential antifungal agents targeting 14 α-demethylase
Deshmukh, Tejshri R.,Jadhav, Rohit G.,Khedkar, Vijay M.,Sangshetti, Jaiprakash N.,Sarkate, Aniket P.,Shingate, Bapurao B.,Tiwari, Shailee V.
supporting information, p. 13104 - 13118 (2021/08/03)
The search for potent therapeutic agents has prompted the design and synthesis of a library of twenty-six aryloxy-tethered and amide-linked symmetrical 1,2,3-triazoles (8a-z) using a copper(i)-catalyzed click chemistry approach. All the synthesized compounds have been screened for theirin vitroantifungal activity against four different fungal strains as well as the enzymatic study for the inhibition of 14 α-demethylase enzyme. The bioactivity results show that most of the synthesized compounds were found to be better antifungal agents as compared to Miconazole. Among them, compound8ashowed the most promising antifungal activity against all the tested fungal strains. Furthermore, the enzymatic study reveals that compounds8iand8oare the most promising inhibitors of the 14 α-demethylase enzyme. In support of these results, the molecular docking study of the synthesized molecules against the sterol 14 α-demethylase (CYP51) could provide the structural basis for the antifungal activity. These compounds have also been analyzed for the ADME properties.
New Mercaptoacetamide Derivatives: Synthesis and Assessment as Antimicrobial and Antimycobacterial Agents
Hashim, Syed Riaz,Hegde, Rahul Rama,Pal, Dilipkumar,Rani, Priyanka
, p. 715 - 723 (2021/10/27)
During last few years, the frightening elevation of bacterial resistance was accompanied by dramatic decline in recent treatments of infectious diseases, which became a point of anxiety for healthcare industries. MDR and XDR strains of Mycobacterium tuberculosis (Mtb) result in the tuberculosis. In this regard, herein, a series of new mercaptoacetamide derivatives were synthesized via multipot synthetic pathway and the rationale was the appraisal of bioactivity in compact heteronuclei and their assessment as potential antimicrobial and antimycobacterial agents against virulent strain of Mtb, H37Ra for structure–activity relationship (SAR) studies. The inhibition zones of compounds 4c and 4e were found to be nearest to that of standard drug Ciprofloxacin, while compounds 4h and 4j were mild to moderately active against Gram positive bacteria (Staphylococcus aureus, Streptococus pneumonia) and Gram negative bacteria (Pseudomonas aeruginosa, Salmonella typhimurium and Escherichia coli). MIC90 assays indicated that new mercaptoacetamides did not exhibit in vitro activity against Mtb in contrast to Rifampicin and Streptomycin, first-line antimycobacterial chemotherapeutic agents. According to the present study, it was concluded that mercaptoacetamides of the new series succeeded as antimicrobial agents but could not develop as potential lead compounds against Mtb when tested in concentrations of 50, 25, 12.5 and 6.25 μg/mL.
Synthesis and biological evaluation of 1,2,3-triazole tethered thymol-1,3,4-oxadiazole derivatives as anticancer and antimicrobial agents
Ahmad, Abrar,Alam, Mohammad Mahboob,Alfaifi, Sulaiman Y. M.,Alghamdi, Abdullah A. A.,Ali, Nada M.,Almalki, Abdulraheem S. A.,Alsharif, Meshari A.,Elhenawy, Ahmed A.,Malebari, Azizah M.,Nazreen, Syed
, (2021/10/05)
A library of 1,2,3-triazole-incorporated thymol-1,3,4-oxadiazole derivatives (6–18) hasbeen synthesized and tested for anticancer and antimicrobial activities. Compounds 7, 8, 9, 10, and 11 exhibited significant antiproliferative activity. Among these act
Synthesis of Some New Acetanilide Derivatives as COX Inhibitors and Assessment of Analgesic/Anti-Inflammatory Activities
Kumar, Arvind,Mishra, Arun K.,Singh, Rajib Kumar
, p. 1475 - 1487 (2022/01/24)
The purpose of the present research was to synthesize a new series of acetanilide derivatives that would have analgesic and anti-inflammatory properties in laboratory animals (rats). IR spectroscopy, 1HNMR spectroscopy and Mass spectroscopy wer
