33863-86-4Relevant articles and documents
Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates
Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul
supporting information, p. 5022 - 5037 (2021/05/04)
Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.
Design and synthesis of N-(3-sulfamoylphenyl)amides as Trypanosoma brucei leucyl-tRNA synthetase inhibitors
Li, Zezhong,Xin, Weixiang,Wang, Qing,Zhu, Mingyan,Zhou, Huchen
, (2021/03/16)
The protozoan parasite Trypanosoma brucei (T. brucei) causes human African trypanosomiasis (HAT), which is a fatal and neglected disease in the tropic areas, and new treatments are urgently needed. Leucyl-tRNA synthetase (LeuRS) is an attractive target for the development of antimicrobial agents. In this work, starting from the hit compound thiourea ZCL539, we designed and synthesized a series of amides as effective T. brucei LeuRS (TbLeuRS) synthetic site inhibitors. The most potent compounds 74 and 91 showed IC50 of 0.24 and 0.25 μM, which were about 700-fold more potent than the starting hit compound. The structure-activity relationship was also discussed. These compounds provided a new scaffold and lead compounds for further development of antitrypanosomal agents.
Spiropyrane derivative with color, fluorescence and liquid crystal property triple switching effects as well as preparation method and application thereof
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Paragraph 0111-0115; 0120; 0123-0128; 0149-0152, (2021/06/26)
The invention discloses a spiropyrane derivative with color, fluorescence and liquid crystal property triple switching effects as well as a preparation method and application of the spiropyrane derivative. The spiropyrane derivative is prepared by esterification reaction of 1',3',3'-trimethyl-6-nitrospiro[benzopyran-2,2'-dihydroindole]-5', 8-diol and alkyl / alkoxy substituted benzoic acid with alkyl / alkoxy group at para-position or acrylate / methacrylate group at the chain end. The spiropyran derivative is used as a molecular switch in a smart material. The spiropyran derivative has responsiveness to light, heat, pH value and force, has triple switchable effects of color, fluorescence and liquid crystal property, has significant difference in response behaviors in different chemical environments, and is suitable for being used as a molecular switch in an intelligent material.
Synthesis and molecular docking studies of some novel antimicrobial benzamides
Acar, Cemre,Yal??n, Gozde,Ertan-Bolelli, Tu?ba,Kaynak Onurda?, Fatma,?kten, Suzan,?ener, Funda,Y?ld?z, ?lkay
, (2019/11/19)
Common use of classical antibiotics has caused to the growing emergence of many resistant strains of pathogenic bacteria. Therefore, we aimed to synthesize a number of N-(2-hydroxy-(4 or 5)-nitrophenyl)benzamide derivatives as a new class of antimicrobial compounds. Moreover, our second goal is to predict the interaction between active structures and enzymes (DNA –gyrase and FtsA) in the binding mode. In this study, thirteen N-(2-hydroxy-(4 or 5-nitrophenyl)-substituted-benzamides were synthesized and determined for their antimicrobial activity using the microdilution method. According to this work, none of the compounds showed any activity against Candida albicans and its clinical isolate. Some of the benzamides (4N1, 5N1, 5N2) displayed very significant activity against Staphylococcus aureus and MSSA with 4 μg/ml MIC value, even they were found to be more potent than ceftazidime. 4N1 was also found to be more effective than gentamicin against Enterococcus faecalis clinical isolate. Molecular docking studies revealed that 4N1, 5N1, and 5N2 showed a good interactions with DNA-gyrase. Moreover, 5N1 has interacted with FtsA enzyme in the binding mode, as well. Only compound 5N4 displayed very good activity against Escherichia coli ATCC 25922. These findings showed us that 4N1, 5N1, 5N2, and 5N4 could be lead compounds to discover new antibacterial candidates against multidrug-resistant strains.
Synthesis and characterization of novel rod-like ester-based liquid crystalline homologous series: Effect of tert-butyl tail on mesomorphism
Thakur, Shavi,Patel, Hemant N.
, p. 76 - 89 (2021/04/14)
A new rod-like homologous series consisting twelve compounds with central ester linkage and terminal tert-butyl group, tert-butyl [4-(4’-n-alkoxybenzoyloxy)benzoates] has been synthesized and characterized through standard spectroscopic techniques like UV, FT-IR, 1HNMR, DSC, POM, and XRD. Methoxy and ethoxy derivatives are nonmesogenic. Nematic mesophase commences as enantiotropy from propyloxy derivative and persists up to the octadecyloxy derivatives. Smectic A mesophase commences as monotropy from propyloxy to the octadecyloxy derivatives. The mesomorphic properties of present series are compared with other structurally related series to evaluate the effect of terminal tert-butyl group on mesomorphism. Two derivatives are subjected to in?vitro antimicrobial activity.
Dependence of mesomorphism on terminal polar group in novel azoester series
Kher, Seema N.,Prajapati,Makwana,Chandra, Raviprakash S.
, p. 44 - 53 (2019/10/14)
Novel homologous series 4-(4′-n-alkoxy benzoyloxy) napthyl azo 4″–bromo benzenes, consisted of 11 members of a series. All the 11 members (ethoxy to hexadecyloxy) except hexadecyloxy are only enantiotropically nematogenic without exhibition of any smectogenic character. Transition temperatures and the textures are determined by an optical polarizing microscopy equipped with a heating stage. Textures of a nematic phase are threaded or schlieren. Analytical and spectral data supported the molecular structure of homologs. Transition curves viz., solid-nematic and nematic-isotropic showing phase behavior of the mesophase in a phase diagram behave in normal manner. Alternation of transition temperatures is exhibited by N–I transition curve. Thus, novel series is entirely nematogenic and high ordered melting type. Thus, synthesis of a novel azoester homologous series is carried out with a view to understand and establish the effect of molecular structure on Liquid crystal (LC) behaviors of a substance.
Identification of Anti-Mycobacterial Biofilm Agents Based on the 2-Aminoimidazole Scaffold
Nguyen, T. Vu,Minrovic, Bradley M.,Melander, Roberta J.,Melander, Christian
, p. 927 - 937 (2019/03/26)
Tuberculosis (TB) remains a significant global health problem for which new therapeutic options are sorely needed. The ability of the causative agent, Mycobacterium tuberculosis, to reside within host macrophages and form biofilm-like communities contributes to the persistent and drug-tolerant nature of the disease. Compounds that can prevent or reverse the biofilm-like phenotype have the potential to serve alongside TB antibiotics to overcome this tolerance, and decrease treatment duration. Using Mycobacterium smegmatis as a surrogate organism, we report the identification of two new 2-aminoimidazole compounds that inhibit and disperse mycobacterial biofilms, work synergistically with isoniazid and rifampicin to eradicate preformed M. smegmatis biofilms in vitro, are nontoxic toward Galleria mellonella, and exhibit stability in mouse plasma.
Structure-Function Evaluation of Imidazopyridine Derivatives Selective for δ-Subunit-Containing γ-Aminobutyric Acid Type A (GABAA) Receptors
Yakoub, Kirsten,Jung, Sascha,Sattler, Christian,Damerow, Helen,Weber, Judith,Kretzschmann, Annika,Cankaya, Aylin S.,Piel, Markus,R?sch, Frank,Haugaard, Anne S.,Fr?lund, Bente,Schirmeister, Tanja,Lüddens, Hartmut
, p. 1951 - 1968 (2018/03/21)
δ-Selective compounds 1 and 2 (DS1, compound 22; DS2, compound 16) were introduced as functionally selective modulators of δ-containing GABA type A receptors (GABAAR). In our hands, [3H]EBOB-binding experiments with recombinant GABAAR and compound 22 showed no proof of δ-selectivity, although there was a minimally higher preference for the α4β3δ and α6β2/3δ receptors with respect to potency. In order to delineate the structural determinants of δ preferences, we synthesized 25 derivatives of DS1 and DS2, and investigated their structure-activity relationships (SAR). Four of our derivatives showed selectivity for α6β3δ receptors (29, 38, 39, and 41). For all of them, the major factors that distinguished them from compound 22 were variations at the para-positions of their benzamide groups. However, two compounds (29 and 39), when tested in the presence of GABA, revealed effects at several additional GABAAR. The newly synthesized compounds will still serve as useful tools to investigate α6β3δ receptors.
Study of Y-shaped liquid crystalline materials with polar nitro substituent
Dixit, Sandhya
, p. 77 - 84 (2018/06/27)
A new homologous series of Y-shaped liquid crystals namely 4-Nitro-[2′4′bis (4″-n-alkoxybenzoyloxy)] phenyl bisazobenzenes have been synthesized and its thermotropic properties studied on the hot stage of a polarizing microscope. The compounds consist four phenyl rings joined through ester and bisazo linkages with alkoxy and nitro as terminal substituents. The structures of synthesized compounds were confirmed by spectroscopic techniques such as FTIR, 1HNMR as well as elemental analysis. The compounds were found to exhibit enantiotropic nematic and smectic mesophases. The role of molecular shape, size and polarity of functional groups in the mesophases formation is discussed.
Mesomorphism dependence on terminal polar group in the nonlinear novel azoester series
Kher, Seema N.,Prajapati,Chandra, Raviprakash S.,Makwana
, p. 1 - 9 (2019/02/24)
Synthesis of a novel azoester homologous series is carried out with a view to understand and establish the effect of molecular structure on liquid crystal (LC) behaviors of a substance. Novel series consists of ten LC substances. All the homologs are enantiotropically nematogenic without exhibition of smectic property. Transition and melting temperatures, textures of LC are determined by an optical polarizing microscopy equipped with a heating stage. Textures of nematic phase are threaded or schlieren. Transition curves of a phase diagram behaved in normal manner. Nematic–isotropic transition curve exhibited odd–even effect. Analytical and spectral data supported and confirmed the structures of homologues.
