2687-43-6Relevant academic research and scientific papers
Synthesis and stereoisomerization of 2-(1-alkoxyimino-2,2,2-trifluoroethyl) -5-trimethylsilylfurans
Melnik,Vorona,Veinberg,Popelis,Ignatovich,Lukevics
, p. 718 - 721 (2005)
2-(1-Alkoxyimino-2,2,2-trifluoroethyl)-5-trimethylsilylfurans were synthesized by the condensation of 2-(trifluoroacetyl)-5-trimethylsilylfuran with alkoxyamines. According to 1H and 19F NMR spectroscopic data, the alkoxyimino group in the E-isomers descreens the H-3 and H-4 protons of the furan ring more strongly than in the Z-isomers, shifting their signals downfield. The fluorine atoms of the α-trifluoromethyl group in the Z-isomer are characterized by a downfield shift in relation to the E-isomer. 2005 Springer Science+Business Media, Inc.
Electrochemical access to benzimidazolone and quinazolinone derivatives: Via in situ generation of isocyanates
Saha, Debarshi,Taily, Irshad Maajid,Naik, Sumitra,Banerjee, Prabal
, p. 631 - 634 (2021/01/29)
Isocyanates are the key intermediates for several organic transformations towards the synthesis of diverse pharmaceutical targets. Herein, we report the development of an oxidant-free protocol for electrochemical in situ generation of isocyanates. This strategy highlights expedient access to benzimidazolones and quinazolinones and eliminates the need for exogenous oxidants. Furthermore, detailed mechanistic studies provide strong support towards our hypothesis of in situ isocyanate generation. This journal is
Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains
Akunuri, Ravikumar,Veerareddy, Vaishnavi,Kaul, Grace,Akhir, Abdul,Unnissa, Tanveer,Parupalli, Ramulu,Madhavi,Chopra, Sidharth,Nanduri, Srinivas
supporting information, (2021/08/27)
Infections caused due to multidrug resistant organisms have emerged as a constant menace to human health. Even though numerous antibiotics are currently available for treating infectious diseases, a great number of bacterial strains have acquired resistance to many of them. Among these, infections caused due to Staphylococcus aureus are predominant in adult and paediatric population. Indole is a prominent chemical scaffold found in many pharmacologically active natural products and synthetic drugs. A number of oxime ether containing compounds have attracted attention of researchers owing to their interesting biological properties. Current work details the synthesis of indole containing oxime ether derivatives and their evaluation for antimicrobial activity against a panel of bacterial and mycobacterial strains. Synthesized compounds demonstrated good to moderate activity against drug-resistant S. aureus including resistant to vancomycin. Among all, compound 5h was found to possess potent activity against susceptible as well as MRSA and VRSA strains of S. aureus with MIC of 1 μg/mL and 2–4 μg/mL respectively. In addition, compound 5h was found to be non-toxic to Vero cells and exhibited good selectivity index of >40. Further, 5h, E-9a and E-9b possessed good biofilm inhibition against S. aureus. With these assuring biological properties, synthesized compounds could be potential prospective antimicrobial agents.
Preparation method of benzyloxyamine hydrochloride
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Paragraph 0059-0061; 0064, (2021/04/14)
The invention discloses a preparation method of benzyloxyamine hydrochloride. The preparation method comprises the following steps: (1) dispersing ketoxime 2 and alkali metal hydroxide into a mixed solvent of dimethylacetamide and water at the temperature of 50-55 DEG C and the stirring speed of 100-120 rpm; (2) dropwise adding a benzyl halide compound 1 into a dispersion body obtained in the step (1), reacting for 130-140 minutes at the temperature of 60-65 DEG C after dropwise adding is completed, then cooling to room temperature, adding water, extracting by using normal hexane, and distilling an organic phase under reduced pressure to obtain a product 3; and (3) adding the product 3 obtained in the step (2) into a mixed solution of methanol and a hydrochloric acid solution with the mass concentration of 38% , reacting for 200-220 minutes at the temperature of 35-40 DEG C and at the stirring speed of 80-100 rpm, distilling under reduced pressure until a solid is separated out, cooling to room temperature, washing the solid with petroleum ether, and drying to obtain the target product 4-benzyloxyamine hydrochloride. According to the preparation method, the total yield can reach 95% or above, and the product purity can reach 99% or above.
Structure-activity relationships of pyrimidine nucleotides containing a 5′-α,β-methylene diphosphonate at the P2Y6 receptor
Dobelmann, Clemens,Gopinatth, Varun,Jacobson, Kenneth A.,Jain, Shanu,Junker, Anna,Oliva, Paola,Phung, Ngan B.,Scortichini, Mirko,Toti, Kiran S.
supporting information, (2021/06/15)
The Gq-coupled P2Y6 receptor (P2Y6R) is a component of the purinergic signaling system and functions in inflammatory, cardiovascular and metabolic processes. UDP, the native P2Y6R agonist and P2Y14R partial agonist, is subject to hydrolysis by ectonucleotidases. Therefore, we have synthesized UDP/CDP analogues containing a stabilizing α,β-methylene bridge as P2Y6R agonists and identified compatible affinity-enhancing pyrimidine modifications. A distal binding region on the receptor was explored with 4-benzyloxyimino cytidine 5′-diphosphate analogues and their potency determined in a calcium mobilization assay. A 4-trifluoromethyl-benzyloxyimino substituent in 25 provided the highest human P2Y6R potency (MRS4554, 0.57 μM), and a 5-fluoro substitution of the cytosine ring in 28 similarly enhanced potency, with >175- and 39-fold selectivity over human P2Y14R, respectively. However, 3-alkyl (31–33, 37, 38), β-D-arabinofuranose (39) and 6-aza (40) substitution prevented P2Y6R activation. Thus, we have identified new α,β-methylene bridged N4-extended CDP analogues as P2Y6R agonists that are highly selective over the P2Y14R.
Vinylogous Aza-Michael Addition of Urea Derivatives with p-Quinone Methides Followed by Oxidative Dearomative Cyclization: Approach to Spiroimidazolidinone Derivatives
Kaur, Navpreet,Singh, Priyanka,Banerjee, Prabal
supporting information, p. 2813 - 2824 (2021/04/21)
Herein, we report an efficient protocol for the synthesis of spiro-imidazolidinone-cyclohexadienones from p-quinone methides (p-QMs) and dialkyloxy ureas under mild conditions. The strategy follows a two-step process involving an initial vinylogous conjugate addition of urea derivatives to p-QMs, followed by oxidative dearomative cyclization of open-chain product to the projected spiro-imidazolidinones. This protocol exhibits good functional group tolerance and provides a straightforward method to access spiro-imidazolidinone-cyclohexadienones. In follow-up chemistry, we have shown the debenzylation of spiroimidazolidinones to give N-hydroxycyclic ureas. (Figure presented.).
Design, synthesis and evaluation of wound healing activity for β-sitosterols derivatives as potent Na+/K+-ATPase inhibitors
Cui, Shaoyu,Jiang, Hongli,Chen, Lei,Xu, Jian,Sun, Wenzhuo,Sun, Haopeng,Xie, Zijian,Xu, Yunhui,Yang, Fubai,Liu, Wenyuan,Feng, Feng,Qu, Wei
, (2020/01/31)
β-Sitosterols, is a common steroid that can be identified in a variety of plants and their efficacy in promoting wound healing has been demonstrated. Na+/K+-ATPase, more than a pump, its signal transduction function for involvement in cell growth regulation attracts widespread concern. The Na+/K+-ATPase/Src receptor complex can serve as a receptor involved in multiple signaling pathways including promoting wound healing pathways. To finding potent accelerating wound healing small molecular, we choose the high inhibitory activity of Na+/K+-ATPase and non-cardiotoxic natural compound, β-sitosterol as the substrate. A series of β-sitosterol derivatives were designed, synthesized and evaluated as potential Na+/K+-ATPase inhibitors. Among them, compounds 31, 47, 49, showed improved inhibitory activity on Na+/K+-ATPase, with IC50 value of 3.0 μM, 3.4 μM, 2.2 μM, which are more potent than β-sitosterol with IC50 7.6 μM. Especially, compound 49 can induce cell proliferation, migration and soluble collagen production in L929 fibroblasts. Compared to model, compound 49 can accelerate wound healing in SD rats. Further studies indicated that 49 can activate the sarcoma (Src), uptake the protein kinase B (Akt), extracellular signal-regulated kinase (ERK) proteins expression in a concentration dependent manner. Finally, binding mode of compound 49 with Na+/K+-ATPase was studied, which provides insights into the determinants of potency and selectivity. These results proved β-stitosterol derivative 49 can serve as an effective inhibitor of Na+/K+-ATPase and potential candidate for accelerating wound healing agents.
Palladium-catalyzed regio- And stereoselective access to allyl ureas/carbamates: Facile synthesis of imidazolidinones and oxazepinones
Banerjee, Prabal,Saha, Debarshi,Taily, Irshad Maajid
, p. 6564 - 6570 (2020/11/10)
Typically, transition metal catalysis enforces the stereodefined outcome of a reaction. Here we disclose the palladium-catalyzed regio- and stereoselective access to allylic ureas/carbamates and their further exploitation to diverse cyclic structures under operationally simple reaction conditions. This protocol features palladium-catalyzed decarboxylative amidation of highly modular VECs with good to excellent yield, minimal waste production, wide substrate scope, and low catalyst loading. In follow-up chemistry, we demonstrated the debenzylation of vinylic imidazolidinones to N-hydroxycyclic ureas and regioselective derivatization towards the facile synthesis of halohydrins and oxiranes under mild reaction conditions in good to excellent yields. This journal is
[3+3] Annulation via Ring Opening/Cyclization of Donor–Acceptor Cyclopropanes with (Un)symmetrical Ureas: A Quick Access to Highly Functionalized Tetrahydropyrimidinones
Taily, Irshad Maajid,Saha, Debarshi,Banerjee, Prabal
, p. 7804 - 7813 (2019/12/27)
A mild and straight-forward access to pharmacologically privileged tetrahydropyrimidinones exploiting readily available Donor–Acceptor cyclopropanes (DACs) is reported. This methodology involves the Lewis acid catalyzed synthesis of uriedo-malonates from (un)symmetrical ureas and DACs followed by I2-base mediated cyclization to their corresponding tetrahydropyrimidinones. The cyclization protocol involves nucleophilic attack of the nitrogen of urea on the newly generated electrophilic acceptor end of DAC. The post functionalization offered potential biologically active molecules.
Preparation method of O-benzylhydroxylamine hydrochloride
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Paragraph 0037-0056, (2019/07/16)
The invention discloses a preparation method of O-benzylhydroxylamine hydrochloride, and relates to the technical field of organic synthesis. The method comprises the following steps: synchronously dropwise adding alcoholic solutions of benzyl halide and alkoxide into oxime to perform a reaction; when no benzyl halide exists in the reaction system, carrying out solid-liquid separation, dropwise adding dilute hydrochloric acid for carrying out hydrolytic rectification, and distilling while dropwise adding the dilute hydrochloric acid to separate out ketone; concentrating the reaction solution and separating out O-benzylhydroxylamine hydrochloride; and drying the benzylamine hydrochloride to obtain an O-benzylhydroxylamine hydrochloride pure product. Oxime is used as a raw material, and thefinally generated ketone or aldehyde can also be recycled to synthesize corresponding oxime. According to the method, the atom utilization rate is improved, the production cost of the product is reduced, the emission of three wastes is reduced, and the goal of green production is achieved.
