3943-74-6Relevant articles and documents
Hydroquinone glycosides from leaves of Myrsine seguinii
Zhong, Xi-Ning,Otsuka, Hideaki,Ide, Toshinori,Hirata, Eiji,Takushi, Anki,Takeda, Yoshio
, p. 2149 - 2153 (1998)
From leaves of Myrsine seguinii, seven hydroquinone glycosides were isolated. By spectroscopic analyses, their structures were elucidated to be arbutin, arbutin 2'- and 6'-O-β-apiofuranosides (seguinosides A and B, respectively), and the benzoyl, p-hydroxybenzoyl, 3-methoxy-4-hydroxybenzoyl and 3,5-dimethoxy-4-hydroxybenzoyl esters of the alcohol hydroxyl group on C- 5'' of arbutin 2'-O-β-apiofuranoside (seguinosides C-F, respectively).
Synthesis, characterization and crystal structure of methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate
Wang, Kai,Zhang, Xiu-Qin,Zhu, Jian,Chen, Qiang,Zhang, Zhong-Qiang,Fan, Li
, p. 2647 - 2650 (2015)
Methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate was synthesized from 4-hydroxy-3-methoxybenzoic acid. Firstly, 4-hydroxy-3-methoxybenzoic acid reacted with methanol in the presence of concentrated sulfuric acid at reflux temperature, then the product of the first step was transformed into benzyl bromide by the process of substitution reaction by using K2CO3. Finally, the product was obtained by nitration reaction with HNO3. The product was characterized by 1H NMR and LC-MS. The crystal structure of compound I was investigated using X-ray diffraction and SHELXTL-97 software. The results indicated that compound I crystallized in the monoclinic system, space group P2(1)/c with a = 5.590(2), b = 17.591 (7), c = 15.427(6) ?, V = 1516.9 (10) ?3; Z 4.
Diploquinones A and B, Two New Phytotoxic Tetrasubstituted 1,4-Naphthoquinones from Diplodia mutila, a Causal Agent of Grapevine Trunk Disease
Reveglia, Pierluigi,Savocchia, Sandra,Billones-Baaijens, Regina,Masi, Marco,Cimmino, Alessio,Evidente, Antonio
, p. 11968 - 11973 (2018)
Two new phytotoxic tetrasubstituted 1,4-naphthoquinones, named diploquinones A and B, were isolated together with vanillic acid from Diplodia mutila (DAR78993), a grapevine pathogen involved in Botryosphaeria dieback in Australia. Diploquinones A and B were characterized as 6,7-dihydroxy-2-methoxy-5-methylnaphthalene-1,4-dione and 3,5,7-trihydroxy-2-methoxynaphthalene-1,4-dione using spectroscopic methods (essentially 1D and 2D 1H and 13C NMR and HR ESIMS). The already known vanillic acid was isolated for the first time as fungal phytotoxin and as metabolite of D. mutila. The three compounds were assayed on detached grapevine leaves (Vitis vinifera cv. Shiraz) at concentrations of 10-3 M and 2.5 × 10-3 M. Vanillic acid showed the highest phytotoxic effect on grapevine leaves irrespective of the tested concentration, while diploquinones A and B showed varying degrees of toxicity.
VISUAL DETECTION OF PBD INDUCED DNA CROSSLINKS
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Page/Page column 37; 38, (2021/04/23)
The present invention relates to the field of oncology, laboratory tools and methods, and especially anti-tumor DNA crosslinking agents. Most patients with advanced solid tumors develop resistance to chemotherapy due to the ability of cancer cells to repair or tolerate sustained DNA damages. The inventors showed that the compounds according to the present invention allow the detection and visualization of alkylated DNA damages induced by PBDs without altering their DNA crosslinking ability. This enables the study of the effect and properties of PBDs. In particular, the present invention relates new derivates of PBD molecules and their synthesis. The present invention also relates to a method for visualizing DNA crosslinking; to a method for assessing the resistance of a tumor to a crosslinking agent and to a method for identifying a molecule or treatment for improving the efficiency of a crosslinking agent.
COMPOSITIONS AND METHODS RELATED TO MOLECULAR CONJUGATION
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Page/Page column 80; 81, (2021/06/11)
The invention relates to activated Michael acceptor (AMA) compounds that can undergo conjugation with biomolecules containing Michael donor moieties, thereby providing plasma-stable antibody-drug conjugates (ADCs). Pharmaceutical compositions of the ADCs are disclosed as well. Also provided herein are a number of applications (e.g., therapeutic applications) in which the compositions are useful.
Transition Metal-Free Regioselective Remote C?H Bond 2,2,2-Trifluoroethoxylation of 8-Aminoquinoline Derivatives at the C5 Position
Ruyet, Louise,Poisson, Thomas,Besset, Tatiana
supporting information, p. 3407 - 3410 (2021/06/28)
The regioselective 2,2,2-trifluoroethoxylation at the C5 position of amides derived from the 8-aminoquinoline has been developed. In the presence of PIDA, an unprecedented and undirected transition metal-free transformation was achieved using the readily available and appealing 2,2,2-trifluoroethanol as the fluorinated source. The selective distal 2,2,2-trifluoroethoxylation of an array of amides was achieved in moderate to good yields (12 examples, up to 61 % yield). This approach provided efficient access to high-value added fluorinated quinoline derivatives, key building blocks for bulk and fine chemical industry.
Novel 4-Anilinoquinazoline Derivatives as Potent Anticancer Agents: Design, Synthesis, Cytotoxic Activity, and Docking Study
Dabirian, Sara,Dogaheh, Mahtab Ghasemi,Ghasemi, Saeed,Moghadam, Fatemeh Azmian,Mojabi, Mohammad,Yousefbeyk, Fatemeh
, p. 730 - 739 (2021/10/29)
The simultaneous inhibition of EGFR and VEGFR-2 is a promising method in cancer treatment. In the present work, several 4-Anilinoquinazoline derivatives encompassing different substitutions at the C-4 and C-7 positions of a quinazoline core were designed, synthesised, and evaluated for their cytotoxicity on A431, HUVEC, and HU02 cell lines. Docking studies were carried out to test the interactions of all synthesised compounds with EGFR and VEGFR-2. Furthermore, a wound healing assay was done for the investigation of cell migration. The most potent compound was 8l followed by the compounds 8i and 8j which showed better cytotoxic activities on A431 and HUVEC cell lines than the standard (Vandetanib). The compounds 8f and 8a represented the best docking energies of 8.99 and 9.35 kcal mol-1 for EGFR and VEGFR, respectively. Moreover, molecular docking studies exhibited that compound 8l showed efficient binding affinity against both EGFR and VEGFR-2. It can bind to these receptors through the formation of essential hydrogen bonds between the quinazoline N1 atom and the Met796 backbone of EGFR and two hydrogen bonds with Cys919 and Thr916 of VEGFR-2 with energies of-7.99 and-7.85 kcal mol-1, respectively. In addition, this compound displayed the highest activity on cell migration and wound healing. Compound 8l with the highest cytotoxic activity can be considered a candidate for further investigation and structural optimisation as an antiproliferative agent.
Design, Synthesis, and Pharmacological Characterization of a Neutral, Non-Prodrug Thrombin Inhibitor with Good Oral Pharmacokinetics
Hillisch, Alexander,Gericke, Kersten M.,Allerheiligen, Swen,Roehrig, Susanne,Schaefer, Martina,Tersteegen, Adrian,Schulz, Simone,Lienau, Philip,Gnoth, Mark,Puetter, Vera,Hillig, Roman C.,Heitmeier, Stefan
, p. 12574 - 12594 (2020/11/13)
Despite extensive research on small molecule thrombin inhibitors for oral application in the past decades, only a single double prodrug with very modest oral bioavailability has reached human therapy as a marketed drug. We have undertaken major efforts to identify neutral, non-prodrug inhibitors. Using a holistic analysis of all available internal data, we were able to build computational models and apply these for the selection of a lead series with the highest possibility of achieving oral bioavailability. In our design, we relied on protein structure knowledge to address potency and identified a small window of favorable physicochemical properties to balance absorption and metabolic stability. Protein structure information on the pregnane X receptor helped in overcoming a persistent cytochrome P450 3A4 induction problem. The selected compound series was optimized to a highly potent, neutral, non-prodrug thrombin inhibitor by designing, synthesizing, and testing derivatives. The resulting optimized compound, BAY1217224, has reached first clinical trials, which have confirmed the desired pharmacokinetic properties.
FUSED HETEROCYCLIC BENZODIAZEPINE DERIVATIVES AND USES THEREOF
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Page/Page column 85, (2020/05/29)
The present disclosure provides compounds and compositions capable of extending lifespan, and methods of use thereof.
SnCl2 catalyzed direct synthesis of pyrroles under aqueous conditions
Tejeswararao,Srikanth
, p. 795 - 802 (2020/03/24)
Synthetic substituted pyrroles are related with interesting biological activities, yet they remain inadequately explored within drug discovery. Late years have seen a growing interest in synthetic approaches that can provide access to structurally novel pyrroles so that the biological usefulness of this compound class can be more fully investigated. Herein, an efficient and versatile practical protocol for the pyrroles using stannous(II) chloride dihydrate as catalyst is described under aqueous conditions at 55 oC in high yields. Also, this method is applicable for the preparation of diversity and oriented pyrrole derivatives.
