841-77-0Relevant articles and documents
Selective naked-eye detection of Hg2+ through an efficient turn-on photoinduced electron transfer fluorescent probe and its real applications
Srivastava, Priyanka,Razi, Syed S.,Ali, Rashid,Gupta, Ramesh C.,Yadav, Suresh S.,Narayan, Gopeshwar,Misra, Arvind
, p. 8693 - 8699 (2014)
A simple molecular fluorescent probe 5 has been designed and synthesized by appending anthracene and benzhydryl moieties through a piperazine bridge. The probe upon interaction with different metal ions showed high selectivity and sensitivity (2 ppb) for Hg2+ through fluorescence "turn-on" response in HEPES buffer. The significant fluorescence enhancement (～10-fold) is attributable to PET arrest due to complexation with nitrogen atoms of the piperazine unit and Hg2+ in 1:2 stoichiometry, in which a naked-eye sensitive fluorescent blue color of solution changed to a blue-green (switched-on). As a proof of concept, promising prospects for application in environmental and biological sciences 5 have been utilized to detect Hg 2+ sensitively in real samples, on cellulose paper strips, in protein medium (like BSA), and intracellularly in HeLa cells. Moreover, the optical behavior of 5 upon providing different chemical inputs has been utilized to construct individual logic gates and a reusable combinational logic circuit. The combinational circuit (switch ON mode; OR logic gate) is easily resettable to the original position (switch OFF mode; INHIBIT logic gate) by applying reset chemical inputs (OH- and PO43-) with great reproducibility.
Indirect reduction of CO2and recycling of polymers by manganese-catalyzed transfer hydrogenation of amides, carbamates, urea derivatives, and polyurethanes
Liu, Xin,Werner, Thomas
, p. 10590 - 10597 (2021/08/20)
The reduction of polar bonds, in particular carbonyl groups, is of fundamental importance in organic chemistry and biology. Herein, we report a manganese pincer complex as a versatile catalyst for the transfer hydrogenation of amides, carbamates, urea derivatives, and even polyurethanes leading to the corresponding alcohols, amines, and methanol as products. Since these compound classes can be prepared using CO2as a C1 building block the reported reaction represents an approach to the indirect reduction of CO2. Notably, these are the first examples on the reduction of carbamates and urea derivatives as well as on the C-N bond cleavage in amides by transfer hydrogenation. The general applicability of this methodology is highlighted by the successful reduction of 12 urea derivatives, 26 carbamates and 11 amides. The corresponding amines, alcohols and methanol were obtained in good to excellent yields up to 97%. Furthermore, polyurethanes were successfully converted which represents a viable strategy towards a circular economy. Based on control experiments and the observed intermediates a feasible mechanism is proposed.
Design, synthesis, and molecular docking study of new piperazine derivative as potential antimicrobial agents
Patil, Mahadev,Noonikara Poyil, Anurag,Joshi, Shrinivas D.,Patil, Shivaputra A.,Patil, Siddappa A.,Bugarin, Alejandro
, (2019/09/06)
Herein, we describe the successful design and synthesis of seventeen new 1,4-diazinanes, compounds commonly known as piperazines. This group of piperazine derivatives (3a-q) were fully characterized by 1H NMR, 13C NMR, FT-IR, and LCMS spectral techniques. The molecular structure of piperazine derivative (3h) was further established by single crystal X-ray diffraction analysis. All reported compounds were evaluated for their antibacterial and antifungal potential against five bacterial (Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, and Pseudomonas aeruginosa) and two fungal strains (Candida albicans and Cryptococcus neoformans). The complete bacterial screening results are provided. As documented, piperazine derivative 3e performed the best against these bacteria. Additionally, data obtained during molecular docking studies are very encouraging with respect to potential utilization of these compounds to help overcome microbe resistance to pharmaceutical drugs, as explicitly noted in this manuscript.
Synthesis and evaluation of potent and selective MGL inhibitors as a glaucoma treatment
Alapafuja, Shakiru O.,Malamas, Michael S.,Shukla, Vidyanand,Zvonok, Alexander,Miller, Sally,Daily, Laura,Rajarshi, Girija,Miyabe, Christina Yume,Chandrashekhar, Honrao,Wood, JodiAnne,Tyukhtenko, Sergiy,Straiker, Alex,Makriyannis, Alexandros
, p. 55 - 64 (2018/11/23)
Monoacylglycerol lipase (MGL) inhibition provides a potential treatment approach to glaucoma through the regulation of ocular 2-arachidonoylglycerol (2-AG) levels and the activation of CB1 receptors. Herein, we report the discovery of new series of carbamates as highly potent and selective MGL inhibitors. The new inhibitors showed potent nanomolar inhibitory activity against recombinant human and purified rat MGL, were selective (>1000-fold) against serine hydrolases FAAH and ABHD6 and lacked any affinity for the cannabinoid receptors CB1 and CB2. Protein-based 1H NMR experiments indicated that inhibitor 2 rapidly formed a covalent adduct with MGL with a residence time of about 6 h. This interconversion process “intrinsic reversibility” was exploited by modifications of the ligand's size (length and bulkiness) to generate analogs with “tunable’ adduct residence time (τ). Inhibitor 2 was evaluated in a normotensive murine model for assessing intraocular pressure (IOP), which could lead to glaucoma, a major cause of blindness. Inhibitor 2 was found to decrease ocular pressure by ～4.5 mmHg in a sustained manner for at least 12 h after a single ocular application, underscoring the potential for topically-administered MGL inhibitors as a novel therapeutic target for the treatment of glaucoma.
Reversed isoniazids: Design, synthesis and evaluation against Mycobacterium tuberculosis
Kumar, Malkeet,Singh, Kawaljit,Ngwane, Andile H.,Hamzabegovic, Fahreta,Abate, Getahun,Baker, Bienyameen,Wiid, Ian,Hoft, Daniel F.,Ruminski, Peter,Chibale, Kelly
supporting information, p. 833 - 844 (2018/01/22)
Novel reversed isoniazid (RINH) agents were synthesized by covalently linking isoniazid with various efflux pump inhibitor (EPI) cores and their structural motifs. These RINH agents were then evaluated for anti-mycobacterial activity against sensitive, isoniazid mono-resistant and MDR clinical isolates of M. tuberculosis and a selected number of compounds were also tested ex vivo for intracellular activity as well as in the ethidium bromide (EB) assay for efflux pump inhibition efficacy. The potency of some compounds against various strains of M. tuberculosis (4a–c, 7 and 8; H37Rv-MIC99 ≤1.25 μM, R5401-MIC99 ≤2.5 μM, X_61-MIC99 ≤5 μM) demonstrated the potential of the reversed anti-TB agent strategy towards the development of novel anti-mycobacterial agents to address the rapidly growing issue of resistance. Further, macrophage activity with >90% inhibition by 1a–c and 3b (MIC90 ≤13.42 μM) and inhibition of EB efflux demonstrated by these compounds are encouraging.
Hydrogenated acridine derivative and its application
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Paragraph 0060; 0061; 0062; 0066, (2016/10/08)
The invention relates to the field of chemical synthesis, and particularly relates to a compound with the general formula being Y-L-X and an application of the compound serving as a calcium channel blocking agent or/and an acetylcholinesterase inhibitor. The compound with the general formula being Y-L-X can be used for adjusting calcium homeostasis and treating cardiovascular diseases, stroke or dementia.
Continuous-Flow Multistep Synthesis of Cinnarizine, Cyclizine, and a Buclizine Derivative from Bulk Alcohols
Borukhova, Svetlana,Nol, Timothy,Hessel, Volker
, p. 67 - 74 (2016/01/16)
Cinnarizine, cyclizine, buclizine, and meclizine belong to a family of antihistamines that resemble each other in terms of a 1-diphenylmethylpiperazine moiety. We present the development of a four-step continuous process to generate the final antihistamines from bulk alcohols as the starting compounds. HCl is used to synthesize the intermediate chlorides in a short reaction time and excellent yields. This methodology offers an excellent way to synthesize intermediates to be used in drug synthesis. Inline separation allows the collection of pure products and their immediate consumption in the following steps. Overall isolated yields for cinnarizine, cyclizine, and a buclizine derivative are 82, 94, and 87 %, respectively. The total residence time for the four steps is 90 min with a productivity of 2 mmol h-1. The incredible bulk: Bulk alcohols are converted continuously into chlorides using HCl in a microflow. A reaction network that consists of four steps and two inline separations leads to the continuous preparation of cinnarizine, cyclizine, and a buclizine derivative with yields of 82, 94, and 87 %, respectively. The total residence time for the four steps is 90 min with a productivity of 2 mmol h-1.
Synthesis and Anticancer Activity of 1-(1H -Indol-3-yl)-2-(4-diarylmethylpiperazine-1-yl)ethane-1,2-dione Derivatives
Jiang, Jun-Rong,Xu, Feng,Wu, Han-Gui
, (2016/08/04)
Several new 1-(4-diarylmethylpiperazine-1-yl)-2-(1H-indol-3-yl)ethane-1,2-dione derivatives were synthesized by acylation of 1-diarylmethylpiperazine with 2-(1H-indol-3-yl)-2-oxoacetyl chloride. Their structures were confirmed by 1H NMR, IR, mass spectra, and elemental analysis. These compounds were further evaluated for their anticancer activity, and most of them were found to have moderate-to-potent antiproliferative activities against Hela, A-549, and ECA-109 cancer cell lines in vitro.
CdS nanocapsules and nanospheres as efficient solar light-driven photocatalysts for degradation of Congo red dye
Khan, Azam,Zia-ur-Rehman,Rehman, Muneeb-ur-,Khan, Rajwali,Zulfiqar,Waseem, Amir,Iqbal, Azhar,Shah, Zawar Hussain
, p. 33 - 41 (2016/08/18)
CdS-1 (nanosphers) and CdS-2 (nanocapsule), were synthesized via green synthetic route without using any toxic surfactants by thermolysis of bis(4-benzhydrylpiperazine-1-carbodithioate-κ2 S, S?)cadmium(II) (1) and bis (4-benzylpipera-zine-1-carbodithioate-κ2 S, S?)cadmium(II) (2), respectively in the presence of ethylenediamine as a solvent. The nanoparticles were characterized by TEM, XRD, SEM, FT-IR UV–Visible and Fluorescence spectroscopy. The TEM results showed the formation of nanospheres (CdS-1) and nanocapsules (CdS-2) from complexes 1 and 2, respectively. Both CdS nanoparticles (NPs) have hexagonal crystal phase and a band gap value in the visible region as confirmed by the XRD and UV–Visible spectra, respectively. The photoluminescence (PL) data revealed that CdS-2 has longer recombination time of photo-injected electron hole pairs than CdS-1. The similar FT-IR spectra for both CdS NPs, and different HOMO-LUMO gap values for complexes {4.8187?eV (1) and CdS-2 4.7504?eV (2)} as predicted by DFT calculations suggest that stability of complexes play a key role in controlling morphology. Furthermore, the visible light driven photocatalytic degradation of Congo red dye was observed higher for nanocapsules than nanospheres due to a longer recombination time of photo-injected electron hole pairs.
Chrysin-piperazine conjugates as antioxidant and anticancer agents
Patel, Rahul V.,Mistry, Bhupendra,Syed, Riyaz,Rathi, Anuj K.,Lee, Yoo-Jung,Sung, Jung-Suk,Shinf, Han-Seung,Keum, Young-Soo
, p. 166 - 177 (2016/05/24)
Synthesis of 7-(4-bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one intermediate treating chrysin with 1,4-dibromobutane facilitated combination of chrysin with a wide range of piperazine moieties which were equipped via reacting the corresponding amines with bis(2-chloroethyl)amine hydrochloride in diethylene glycol monomethyl ether solvent. Free radical scavenging potential of prepared products was analyzed in vitro adopting DPPH and ABTS bioassay in addition to the evaluation of in vitro anticancer efficacies against cervical cancer cell lines (HeLa and CaSki) and an ovarian cancer cell line SK-OV-3 using SRB assay. Bearable toxicity of 7a-w was examined employing Madin-Darby canine kidney (MDCK) cell line. In addition, cytotoxic nature of the presented compounds was inspected utilizing Human bone marrow derived mesenchymal stem cells (hBM-MSCs). Overall, 7a-w indicated remarkable antioxidant power in scavenging DPPH+ and ABTS++, particularly analogs 7f, 7j, 7k, 7l, 7n, 7q, 7v, 7w have shown promising free radical scavenging activity. Analogs 7j and 7o are identified to be highly active candidates against HeLa and CaSki cell lines, whereas 7h and 7l along with 7j proved to be very sensitive towards ovarian cancer cell line SKOV-3. None of the newly prepared scaffolds showed cytotoxic nature toward hBM-MSCs cells. From the structure-activity point of view, nature and position of the electron withdrawing and electron donating functional groups on the piperazine core may contribute to the anticipated antioxidant and anticancer action. Different spectroscopic techniques (FT-IR, 1H NMR, 13C NMR, Mass) and elemental analysis (CHN) were utilized to confirm the desired structure of final compounds.
