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22118-09-8Relevant articles and documents
Synthesis and characterization of DOTA-mono-adamantan-1-ylamide
Wan, Fuxian,Liu, Mingjie,Zhang, Junzheng,Li, Ying,Jiang, Lin
, p. 5109 - 5119 (2015)
A novel chelator of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) functionalized by adamantane was synthesized by nucleophilic substituted reaction of 1,4,7-Tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane (5) and N-(adamantan-1-yl) bromoacetamide (2). The intermediates and target compound (7) were characterized by fourier transform infrared spectroscopy (FT-IR), 1H nuclear magnetic resonance (NMR), 13C NMR, atmospheric-pressure ionization electrospray mass spectrometry (API-ES-MS), and elemental analysis.
Design, synthesis, and evaluation of fimbrolide-nitric oxide donor hybrids as antimicrobial agents
Kutty, Samuel K.,Barraud, Nicolas,Pham, Amy,Iskander, George,Rice, Scott A.,Black, David Stc.,Kumar, Naresh
, p. 9517 - 9529 (2013)
Fimbrolides from marine algae have shown promising activity against quorum sensing (QS), a chief regulatory and communication system in bacteria controlling biofilm formation and virulence factor. Nitric oxide (NO) at sublethal concentration has also been reported to induce dispersal of bacterial biofilms and increase their susceptibility toward standard biocides and antibiotics. Therefore, the combination of QS inhibitors and NO donors has the potential to control the development of biofilm and promote their dispersion via a nonbactericidal mechanism. Inspired by these ideas, novel fimbrolide-NO donor hybrid compounds were designed and synthesized. Fimbrolide-NO hybrids 6b, 6f, and 14a were found to be particularly effective as antimicrobials compared to the nonhybrid natural fimbrolides as revealed by bioluminescent P. aeruginosa QS reporter assays and biofilm inhibition assays. Significantly, these fimbrolide-NO hybrids represent the first dual-action antimicrobial agent based on the baterial QS inhibition and NO signaling.
Gemfibrozil derivatives as activators of soluble guanylyl cyclase – A structure-activity study
Baker, Hannah,Ferreira, Liam D.,Gayler, Kevin M.,Kane, Robert R.,Karunananthan, Johann W.,Kostyo, Jessica H.,Martin, Emil,Mattke, Jordan,Nguyen, Harold,Plunk, Michael A.,Quintana, Jeremy M.,Sharina, Iraida,Shuda, Mina,Stinchcomb, Alexandra L.
, (2021/08/09)
Previous studies demonstrated that anti-hyperlipidemic drug gemfibrozil acts as NO- and heme-independent activator of NO receptor soluble guanylyl cyclase. A series of new gemfibrozil derivatives were synthesized and evaluated for sGC activation. The structure-activity relationship study identified the positions in gemfibrozil's scaffold that are detrimental for sGC activation and those that are amendable for optimizing modifications. Compared with gemfibrozil, compounds 7c and 15b were more potent activators of cGMP-forming activity of purified sGC and exhibited enhanced relaxation of preconstricted mouse thoracic aorta rings. These studies established the overall framework needed for futher improvement of sGC activators based on gemfibrozil scaffold.
Synthesis and Fungitoxic Evaluation of Acylamino-1,2,4-Triazoles
Kaur, Gurinderjit,Kaur, Harleen,Kaur, Pardeep,Sharma, Sunita,Singh, Ravneet
, p. 389 - 395 (2021/11/22)
Ten different acylamino-1,2,4-triazoles were prepared by the reaction of differently substituted benzoyl chlorides and acetyl chlorides with 4-amino-1,2,4-triazole using catalytic amount of triethylamine. The synthesized compounds were characterized using UV, 1H-nuclear magnetic resonance spectroscopy, and infrared spectroscopy. All the compounds were tested for their fungicidal potential against three fungal species, that is, Fusarium verticillioides, Macrophomina phaseolina, and Rhizoctonia solani using poisoned food technique. The synthesized compounds were tested at various concentrations along with standard carbendazim 50 WP. The amides synthesized by reaction of substituted benzoyl chlorides and 4-amino-1,2,4-triazole exhibited greater fungicidal activity against all the tested fungi as compared to the amides synthesized using substituted acetyl chlorides. Among all the tested compounds, 4-nitro-N-(4-H-1,2,4-triazol-4-yl)benzamide showed the maximum fungicidal activity with the least median effective dose (ED50) values of 100, 93, and 146 μg ml-1 against F verticillioides, M. phaseolina, and R. solani, respectively. All the compounds were found to be less effective than the standard used.
POMALIDOMIDE DERIVATIVE AND PREPARATION METHOD THEREFOR
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Paragraph 0112-0113, (2020/07/14)
Disclosed in the present invention are a Pomalidomide derivative and a preparation method therefor. Specifically, the present invention relates to the Pomalidomide derivative and a stereoisomer thereof, or a pharmaceutically acceptable salt, and applications thereof in the preparation of drugs for treating cancers.
Design, synthesis and biological evaluation of novel acetamide-substituted doravirine and its prodrugs as potent HIV-1 NNRTIs
Wang, Zhao,Yu, Zhao,Kang, Dongwei,Zhang, Jian,Tian, Ye,Daelemans, Dirk,De Clercq, Erik,Pannecouque, Christophe,Zhan, Peng,Liu, Xinyong
, p. 447 - 456 (2019/01/04)
A novel series of acetamide-substituted derivatives and two prodrugs of doravirine were designed and synthesized as potent HIV-1 NNRTIs by employing the structure-based drug design strategy. In MT-4 cell-based assays using the MTT method, it was found that most of the new compounds exhibited moderate to excellent inhibitory potency against the wild-type (WT) HIV-1 strain with a minimum EC50 value of 54.8 nM. Among them, the two most potent compounds 8i (EC50 = 59.5 nM) and 8k (EC50 = 54.8 nM) displayed robust activity against WT HIV-1 with double-digit nanomolar EC50 values, being superior to lamivudine (3TC, EC50 = 12.8 μM) and comparable to doravirine (EC50 = 13 nM). Besides, 8i and 8k shown moderate activity against the double RT mutant (K103N + Y181C) HIV-1 RES056 strain. The HIV-1 RT inhibition assay further validated the binding target. Molecular simulation of the representative compounds was employed to provide insight on their structure-activity relationships (SARs) and direct future design efforts. Finally, the aqueous solubility and chemical stability of the prodrugs 9 and 10 were investigated in detail.
POMALIDOMIDE DERIVATIVES AND THE PREPARING METHOD THEREOF
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Paragraph 0102-0104, (2019/08/01)
The invention relates to pomalidomide derivatives and their stereoisomers or pharmaceutically acceptable salts, and their use in preparing medicaments for treating cancers.
Isoalantolactone derivative, pharmaceutical composition and application thereof
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Paragraph 0014, (2019/02/02)
The invention relates to an isoalantolactone derivative, a pharmaceutical composition and application thereof, especially use of the isoalantolactone derivative shown as formula (I) or a salt pharmaceutical compound thereof in preparation of adjuvant drugs treating cancer, a pharmaceutical composition containing a therapeutically effective amount of isoalantolactone derivative (I) or its salt anda pharmaceutically acceptable carrier or a composition with other anticancer drugs.
Design, synthesis and biological study of potent and covalent HER-2 tyrosine kinase inhibitors with low cytotoxicity in vitro
Jin, Shuyu,Sun, Xiuyun,Liu, Dan,Xie, Hua,Rao, Yu
, p. 1333 - 1345 (2019/05/06)
The discovery and development of a novel HER-2 tyrosine kinase inhibitor for the treatment of HER2-positive breast cancer are presented in this article. EGFR family has been recognized as a crucial meditator in the cancer progression; HER-2 tyrosine kinase was one of the members among them. In the effort to explore potent HER-2 inhibitors, a novel series of 4-anilino-3-cyanoquinoline derivatives have been designed, synthesized and evaluated. Most compounds possessed modest proliferation inhibition on SK-BR-3 cell line and HER-2 kinase. Compound 16 appeared to be the most potent compound (HER-2 kinase IC50: 19.4?nM, SK-BR-3 IC50: 94?nM). In the experiment of cellular cytotoxicity assay, compound 16 shows a much lower cytotoxicity than neratinib on Beas-2b cell line (Human bronchial epithelial cells). In conclusion, compound 16 would be a promising lead compound for further anti-breast cancer drug discovery.
GluN2B subunit targeting central nervous system positron tracer and preparation thereof
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Paragraph 0030-0034; 0042; 0045-0047, (2019/10/15)
The existing GluN2B selective positron tracer has relatively high affinity and selectivity, but does not show ideal tracer properties in an in vivo experiment, has the problems of overquick metabolism, lower brain uptake, undifferentiated distribution in the whole brain, overquick degradation of C-11 labeled probe and off-target phenomenon caused by influence of other target spots in the brain, which limit the further translational research. The invention designs a novel GluN2B subunit targeting central nervous system positron tracer, reduces the metabolism rate of the tracer and prolongs theservice time by utilizing the characteristics that a methylamino structure is stable and not easy to metabolize. Meanwhile, the tracer of the invention is easy to be detected and traced through experiments, and has a better electron tracing effect. In addition, a preparation method provided by the invention is mild in conditions, and can quickly obtain a high-purity C11-labeled tracer injection,so as to effectively solve the problem of overquick degradation of the C-11 labeled probe.
