88349-90-0Relevant academic research and scientific papers
Chemically modified derivatives of the activator compound cloxyquin exert inhibitory effect on TRESK (K2P18.1) background potassium channel
Lengyel, Miklós,Erdélyi, Ferenc,Pergel, Enik?,Bálint-Polonka, ágnes,Dobolyi, Alice,Bozsaki, Péter,Dux, Mária,Király, Kornél,Hegedüs, Tamás,Czirják, Gábor,Mátyus, Péter,Enyedi, Péter
, p. 652 - 660 (2019)
Cloxyquin has been reported as a specific activator of TRESK [TWIK-related spinal cord K1 channel (also known as K2P18.1)] background potassium channel. In this study, we have synthe-tized chemically modified analogs of cloxyquin and tested their effects on TRESK and other K2P channels. The currents of murine K2P channels, expressed heterologously in Xenopus oocytes, were measured by two-electrode voltage clamp, whereas the native background K1 conductance of mouse dorsal root ganglion (DRG) neurons was examined by the whole-cell patch-clamp method. Some of the analogs retained the activator character of the parent compound, but, more interestingly, other derivatives inhibited mouse TRESK current. The inhibitor analogs (A2764 and A2793) exerted state-dependent effects. The degree of inhibition by 100 mM A2764 (77.8% 6 3.5%, n 5 6) was larger in the activated state of TRESK (i.e., after calcineurin-dependent stimulation) than in the resting state of the channel (42.8% 6 11.5% inhibition, n 5 7). The selectivity of the inhibitor compounds was tested on several K2P channels. A2793 inhibited TWIK-related acid-sensitive K1 channel (TASK)-1 (100 mM, 53.4% 6 13, 5%, n 5 5), while A2764 was more selective for TRESK, it only moderately influenced TREK-1 and TWIK-related alkaline pH-activated K1 channel. The effect of A2764 was also examined on the background K1 currents of DRG neurons. A subpopulation of DRG neurons, prepared from wild-type animals, expressed background K1 currents sensitive to A2764, whereas the inhibitor did not affect the currents in the DRG neurons of TRESK-deficient mice. Accordingly, A2764 may prove to be useful for the identification of TRESK current in native cells, and for the investigation of the role of the channel in nociception and migraine.
Synthesis, structure analysis, DFT calculations and energy frameworks of new coumarin appended oxadiazoles, to regress ascites malignancy by targeting VEGF mediated angiogenesis
Banumathi,Jyothi, Mahima,Khamees, Hussien Ahmed,Khanum, Shaukath Ara,Prabhakar, B. T.,Sherapura, Ankith,Zabiulla
, (2021/12/24)
Ascites malignancy is a frequent cause of morbidity and presents significant management problems which occur in many cancers. Angiogenesis plays a major role in the prognosis of ascites tumor through Vascular Endothelial Growth Factor (VEGF). Inhibition o
A New Series of 1,3,4-Oxadiazole Linked Quinolinyl-Pyrazole/Isoxazole Derivatives: Synthesis and Biological Activity Evaluation
Basavanna, V.,Bhadraiah, U. K.,Chandra,Chandramouli, M.,Doddamani, Shridevi,Kempaiah, C.,Lingegowda, N. S.,Ningaiah, S.
, p. 2257 - 2266 (2021/12/23)
Abstract: A series of 1,3,4-oxadiazole bridged pyrazole/isoxazole bearing quinoline derivatives has been designed and synthesized by a clean and convenient method. Structures of the newly synthesized compounds have been confirmed by FTIR, 1H and 13C NMR, and HRMS spectral data. The titled compounds have been evaluated for their molecular docking guided antimicrobial and anti-inflammatory activity. One of 1,3,4-oxadiazole bridged quinolinyl-pyrazole derivatives has interacted efficiently with E. Coli protein (PDB file: 1KZN), and has been characterized by good antimicrobial activity against the majority of the tested pathogens. Another product has exhibited excellent anti-inflammatory activity.
Process Development for the Crop Safener Cloquintocet Acid
Zhang, Chunming,Leng, Ron,Hamilton, Chris,Sheng, Min,Tu, Siyu,Gu, Binghe,Bell, Bruce
, p. 2218 - 2224 (2019/08/26)
A practical one-pot process was developed for (5-chloroquinolin-8-yloxy)acetic acid (CQC acid), known commercially as cloquintocet, a crop safener that is added to various herbicide formulations to reduce crop damage. The process consists of (1) conversion of 5-chloro-8-hydroxyquinoline (5-ChQ) to its corresponding sodium salt 5-ChQ-Na with 50 wt % NaOH in dimethyl sulfoxide (DMSO), (2) alkylation of 5-ChQ-Na with methyl 2-chloroacetate to generate CQC methyl ester (CQC-Me) after removal of water by distillation under reduced pressure, and (3) hydrolysis of CQC-Me with a catalytic amount of 0.1 N HCl (0.5 mol %) or 0.1 N H2SO4 (0.25 mol %) to afford CQC acid in >90% yield with >98% purity. All of the steps were carried out in one pot with only one isolation. Recovery and reuse of DMSO were also demonstrated. Each step/stage of the process was subjected to reactive chemical evaluation by differential scanning calorimetry and/or accelerating rate calorimetry for identification of potential safety hazards.
A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines
Motati, Damoder Reddy,Uredi, Dilipkumar,Watkins, E. Blake
, p. 1782 - 1788 (2018/02/23)
An operationally simple and metal-free protocol for geometrically inaccessible C5-H halogenation of a range of 8-substituted quinoline derivatives has been established. The reaction proceeds under air, with inexpensive and atom economical trihaloisocyanuric acid as a halogen source (only 0.36 equiv.), at room temperature. Exceptionally high generality with respect to quinoline is observed, and in most instances, the reaction proceeded with complete regioselectivity. Quinoline with a variety of substituents at the 8-position gave, exclusively, the C5-halogenated product in good to excellent yields. Phosphoramidates, tertiary amides, N-alkyl/N,N-dialkyl, and urea derivatives of quinolin-8-amine as well as alkoxy quinolines were halogenated at the C5-position via remote functionalization for the first time. This methodology provides a highly economical route to halogenated quinolines with excellent functional group tolerance, thus providing a good complement to existing remote functionalization methods of quinolin-8-amide derivatives and broadening the field of remote functionalization. The utility of the method is further showcased through the synthesis of several compounds of biological and pharmaceutical interest.
Facile synthesis of tricyclic oxazino- or oxazepino-fused tetrahydroquinolines via intramolecular reductive amidation
Mondal, Shyamal,Maity, Arindam,Naskar, Subhendu,Paira, Rupankar,Hazra, Abhijit,Sahu, Krishnendu B.,Saha, Pritam,Das, Saktipada,Banerjee, Sukdeb,Mondal, Nirup B.
experimental part, p. 2079 - 2084 (2011/08/03)
Reductive cyclization of -(8-quinolyloxy)alkyl esters by zinc in acetic acid is shown to constitute a convenient methodology for the synthesis of oxazino- or oxazepino-fused tetrahydroquinolines. It is operationally simple, requires a short reaction time, and provides excellent yields. Georg Thieme Verlag Stuttgart ? New York.
Herbicidal compositions
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, (2008/06/13)
The present invention relates to a herbicidal composition comprising A) one or more sulfonylureas of the formula (I) and/or their salts ?in which R1is C2-C4-alkoxy or CO—Ra, where Raequals OH, C1-C4-alkoxy or NRbRc, in which Rband Rcindependently of one another are identical or different and are H or C1-C4-alkyl, R2is halogen or (A)n—NRdRe, in which n equals zero or1, A is a group CR′R″, in which R′ and R″ independently of one another are identical or different and are H or C1-C4-alkyl, Rdequals H or C1-C4-alkyl and Reis an acyl radical and, in the event that R1equals C2-C4-alkoxy, Remay also be H, R3is H or C1-C4-alkyl, m equals zero or 1, X and Y independently of one another are identical or different and are C1-C6-alkyl, C1-C6-alkoxy or C1-C6-alkylthio, each of the three radicals mentioned being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, C1-C4-alkoxy and C1-C4-alkylthio, or are C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-alkenyloxy or C3-C6-alkynyloxy, preferably C1-C4-alkyl or C1-C4-alkoxy, Z equals CH or N, and B) one or more vegetable oils.
