- UREA, AMIDE, AND SUBSTITUTED HETEROARYL COMPOUNDS FOR CBL-B INHIBITION
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Compounds of formulae (I) and (II), compositions, and methods for use in inhibiting the E3 enzyme Cbl-b in the ubiquitin proteasome pathway are disclosed. The compounds, compositions, and methods can be used to modulate the immune system, to treat diseases amenable to immune system modulation, and for treatment of cells invivo, in vitro, or ex vivo.
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Paragraph 0510
(2021/02/05)
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- Ru-Catalyzed [3 + 2] Cycloaddition of Nitrile Oxides and Electron-Rich Alkynes with Reversed Regioselectivity
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Polarity reversal ("umpolung") of a functional group can override its inherent reactivity and lead to distinct bond-forming modes. Herein we describe a rarely studied cycloaddition between nitrile oxides and electron-rich alkynes with reversed regioselect
- Feng, Qiang,Huang, Hai,Sun, Jianwei
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supporting information
p. 2431 - 2436
(2021/05/05)
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- Dibenzazepine-linked isoxazoles: New and potent class of α-glucosidase inhibitors
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α-Glucosidase inhibition is a valid approach for controlling hyperglycemia in diabetes. In the current study, new molecules as a hybrid of isoxazole and dibenzazepine scaffolds were designed, based on their literature as antidiabetic agents. For this, a series of dibenzazepine-linked isoxazoles (33–54) was prepared using Nitrile oxide-Alkyne cycloaddition (NOAC) reaction, and evaluated for their α-glucosidase inhibitory activities to explore new hits for treatment of diabetes. Most of the compounds showed potent inhibitory potency against α-glucosidase (EC 3.2.1.20) enzyme (IC50 = 35.62 ± 1.48 to 333.30 ± 1.67 μM) using acarbose as a reference drug (IC50 = 875.75 ± 2.08 μM). Structure-activity relationship, kinetics and molecular docking studies of active isoxazoles were also determined to study enzyme-inhibitor interactions. Compounds 33, 40, 41, 46, 48–50, and 54 showed binding interactions with critical amino acid residues of α-glucosidase enzyme, such as Lys156, Ser157, Asp242, and Gln353.
- Umm-E-Farwa,Ullah, Saeed,Khan, Maria Aqeel,Zafar, Humaira,Atia-tul-Wahab,Younus, Munisaa,Choudhary, M. Iqbal,Basha, Fatima Z.
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supporting information
(2021/05/10)
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- Electrochemical synthesis of 1,2,4-oxadiazoles from amidoximes through dehydrogenative cyclization
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A convenient and efficient method for the generation of the iminoxy radical through anodic oxidation was developed for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles fromN-benzyl amidoximes. The transformation proceeds through 1.5-Hydrogen Atom Transfer (1,5-HAT) and intramolecular cyclization. The process features simple operation, mild conditions, broad substrate scope and high functional group compatibility, and provides a facile and practical way for the preparation of 1,2,4-oxadiazoles.
- Hu, Aixi,Jiang, chan,Li, mingfang,Xu, Leitao,Ye, Jiao,Yi, Yangjie
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supporting information
p. 10611 - 10616
(2021/12/27)
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- On the mixed oxides-supported niobium catalyst towards benzylamine oxidation
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A series of mixed oxides-supported niobium-based catalysts has been synthesized and applied towards oxidation reactions of benzylamine derivatives. Under the optimized reaction conditions, the selectivity to oxime enhanced, leading to the main product with up to 72 %. Moreover, even α-substituted benzylamines were well tolerated and led to oximes in good isolated yields. It is important to mention; four equivalents of the harmless and inexpensive hydrogen peroxide were employed as oxidizing agent. Mechanism hypothesis suggested that the reaction proceed to selective benzylamine oxidation into nitroso intermediate, following by formation of the corresponding oxime tautomer mediated by an unstable water produced by NbOx supported catalyst. This consists the first mixed oxides-supported niobium-based catalyst for selective oxidation of benzylamines to oximes.
- Granato, álisson Silva,de Carvalho, Gustavo S. Gon?alves,Fonseca, Carla G.,Adrio, Javier,Leit?o, Alexandre A.,Amarante, Giovanni Wilson
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p. 118 - 125
(2020/09/11)
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- Water mediated procedure for preparation of stereoselective oximes as inhibitors of MRCK kinase
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Stereoselective aldoximes, preferably Z form have been obtained from α-cyano substituted carbonyl conjugated alkenes. This reaction occurs through Michael addition type reaction followed by retro-Knoevenagel reaction without transition-metal catalysis via C–C bond cleavage. These oximes are evaluated against cancer cell lines employing mechanistic study. Two oximes showed significant cytotoxic activity, which through in silico studies were found to inhibit MRCK Kinase, responsible for metastatic spread of cancer mortality.
- Luqman, Suaib,Misra, Krishna,Pandey, Jyoti,Shrivash, Manoj Kumar,Shukla, Akhilesh Kumar,Singh, Shilipi
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- Microwave synthesis method of benzaldoxime compounds
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The invention discloses a microwave synthesis method of benzaldoxime compounds. The method comprises the following steps: dissolving a substituted benzaldehyde, hydroxylamine hydrochloride and an alkaline compound in an organic solvent, placing the formed solution in a microwave reaction kettle for a reaction, spin-drying the solvent after the reaction is finished, conducting mixed extraction withethyl acetate and water, separating an organic phase, carrying out drying with anhydrous sodium sulfate, and successively performing filtering and desolventizing to obtain a benzaldoxime compound. Based on the structure of the substituted benzaldehyde, the substituted benzaldoxime compound is obtained by reacting the aldehyde with hydroxylamine hydrochloride in the microwave reaction kettle. Themethod is simple in process, convenient to operate, short in reaction time and high in yield, meets the requirement for environment friendliness and improves economic benefits.
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Paragraph 0031-0034
(2020/12/08)
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- Cu(II)–metformin immobilized on graphene oxide: an efficient and recyclable catalyst for the Beckmann rearrangement
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Abstract: In this study, for the first time, the copper(II) nanoparticles (NPs) have been immobilized on metformin-functionalized graphene oxide and then its catalytic applications have been investigated in synthesis of amides from aldoximes (Beckmann rearrangement). The chemical structure of prepared catalyst has been characterized by various analyses like FT-IR, TGA, TEM, SEM, EDX, and ICP. All analyses confirm the successful and stable immobilization of copper NPs on functionalized graphene oxide. This synthesized heterogeneous nanocatalyst showed excellent catalytic activity with high product yields and short reaction times. Also, the suggested catalyst could be recycled ten times without a drastic decrease in its catalytic activity. Graphic abstract: [Figure not available: see fulltext.].
- Solaiman Hamed, Ahmed,Mohammad Ali, Ehab
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p. 701 - 714
(2019/11/03)
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- Triazole alcohol derivative as well as preparation method and application thereof
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The invention relates to a triazole alcohol derivative as well as a preparation method and application thereof. The chemical structure of the triazole alcohol derivative is shown as a formula I, R1 represents a benzene ring or a substituted benzene ring, and substituent groups of the substituted benzene ring can be located at all positions of the benzene ring, can be mono-substituted or multi-substituted, and can be selected from a) halogen which is F and Cl; b) an electron withdrawing group which is cyano or trifluoromethyl; c ) a lower alkyl of 1-4 carbon atoms or a halogen substituted loweralkyl; and d) lower alkoxy of 1-4 carbon atoms or halogen substituted lower alkoxy. The compound of the invention has strong antifungal activity, has the advantages of low toxicity, wide antibacterial spectrum and the like, and can be used for preparing antifungal drugs.
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Paragraph 0159-0160
(2020/03/11)
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- SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)
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A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.
- Ding, Chengrong,Ge, Shuting,Wei, Junjie,Zhang, Guofu,Zhao, Yiyong
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p. 17288 - 17292
(2020/05/18)
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- Design, synthesis, and in vitro evaluation of novel triazole analogues featuring isoxazole moieties as antifungal agents
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In order to develop novel antifungal agents, based on our previous work, a series of (2R,3R)-3-((3-substitutied-isoxazol-5-yl)methoxy)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl) butan-2-ol (a1-a26) were designed and synthesized. All of the compounds exhibited good in vitro antifungal activities against eight human pathogenic fungi. Among them, compound a6 showed excellent inhibitory activity against Candida albicans and Candida parasilosis with MIC80 values of 0.0313 μg/mL. In addition, compounds a6, a9, a12, a13 and a14 exhibited moderate inhibitory activities against fluconazole-resistant isolates with MIC80 values ranging from 8 μg/mL to 16 μg/mL. Furthermore, compounds a6, a12 and a23 exhibited low inhibition profiles for CYP3A4. Clear SARs were analyzed, and the molecular docking experiment was carried out to further investigate the relationship between a6 and the target enzyme CYP51.
- Chai, Xiaoyun,Ding, Zichao,Hao, Yumeng,Jiang, Yuanying,Jin, Yongsheng,Ni, Tingjunhong,Wang, Ruilian,Wang, Ruina,Wang, Ting,Xie, Fei,Yu, Shichong,Zhang, Dazhi
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supporting information
(2020/06/17)
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- Unusual Reactivity of 4-Vinyl Isoxazoles in the Copper-Mediated Synthesis of Pyridines, Employing DMSO as a One-Carbon Surrogate
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An efficient protocol for the synthesis of nicotinate derivatives and tetrasubstituted pyridines through a copper-mediated cleavage of isoxazoles has been developed. The highlight of the work is the observation of an unusual reactivity of 4-vinyl isoxazoles under the reaction conditions. DMSO serves as a one-carbon surrogate generating an active methylene group during the reaction to form two C-C bonds. This protocol provides a facile and an expeditious approach for the assembly of densely substituted N-heterocyclic compounds.
- Kumar, Pravin,Kapur, Manmohan
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supporting information
p. 5855 - 5860
(2020/07/30)
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- Design, synthesis of novel 4,5-dihydroisoxazole-containing benzamide derivatives as highly potent FtsZ inhibitors capable of killing a variety of MDR Staphylococcus aureus
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Antibiotic resistance among clinically significant bacterial pathogens, such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant S. aureus (VRSA) is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. As a part of continuing effort to develop antibacterial agents, we rationally designed and synthesized two series of 4,5-dihydroisoxazol-5-yl and 4,5-dihydroisoxazol-3-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compound A16 possessing the 4,5-dihydroisoxazol-5-yl group showed outstanding antibacterial activity (MIC, ≤0.125–0.5 μg/mL) against various testing strains, including methicillin-resistant, penicillin-resistant and clinical isolated S. aureus strains. Besides, further mouse infection model revealed that A16 could be effective in vivo and non-toxic to Hela cells. Finally, a detailed discussion of structure-activity relationships was conducted, referring to the docking results. It is worth noting that substituting a 4,5-dihydroisoxazole ring for the isoxazole ring not only broadened the antibacterial spectrum but also resulted in a significant increase in antibacterial activity against S. aureus strains. Taken together, these results suggest a promising chemotype for the development of new FtsZ-targeting bactericidal agents.
- Song, Di,Bi, Fangchao,Zhang, Nan,Qin, Yinhui,Liu, Xingbang,Teng, Yuetai,Ma, Shutao
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supporting information
(2020/09/11)
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- One-pot Synthesis of Some Novel Xanthine Derived Isoxazoles as Potent Antibacterial Agents
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In search of better antibacterial agents, a series of novel xanthine derived 3,5-disubstituted isoxazole derivatives were synthesized (3a-3j) in one-pot using 8-chloro-1,3-dimethyl-7-(prop-2-yn-1-yl)-1H-purine-2,6(3H,7H)-dione and aromatic aldehydes and f
- Vidya
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p. 551 - 557
(2021/02/02)
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- Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles
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Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, NH 2 OH, and then NCS, followed by reaction with alkynes in the presence of Et 3 N. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, PhNHNH 2, and then NCS and decyl methyl sulfide, followed by reaction with alkynes in the presence of Et 3 N. Thus, both 3-aryl- and 3-alkylisoxazoles, and 3-aryl- and 3-alkylpyrazoles could be prepared from readily available primary alcohols in one pot under transition-metal-free conditions.
- Kobayashi, Eiji,Togo, Hideo
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p. 3723 - 3735
(2019/09/30)
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- Synthesis and in vitro evaluation of neutral aryloximes as reactivators of Electrophorus eel acetylcholinesterase inhibited by NEMP, a VX surrogate
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Casualties caused by nerve agents, potent acetylcholinesterase inhibitors, have attracted attention from media recently. Poisoning with these chemicals may be fatal if not correctly addressed. Therefore, research on novel antidotes is clearly warranted. Pyridinium oximes are the only clinically available compounds, but poor penetration into the blood-brain barrier hampers efficient enzyme reactivation at the central nervous system. In searching for structural factors that may be explored in SAR studies, we synthesized and evaluated neutral aryloximes as reactivators for acetylcholinesterase inhibited by NEMP, a VX surrogate. Although few tested compounds reached comparable reactivation results with clinical standards, they may be considered as leads for further optimization.
- Cavalcante, Samir F. de A.,Kitagawa, Daniel A.S.,Rodrigues, Rafael B.,Bernardo, Leandro B.,da Silva, Thiago N.,dos Santos, Wellington V.,Correa, Ana Beatriz de A.,de Almeida, Joyce S.F.D.,Fran?a, Tanos C.C.,Ku?a, Kamil,Simas, Alessandro B.C.
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- A Deoximation Method for Deprotection of Ketones and Aldhydes Using a Graphene-Oxide-Based Co-catalysts System
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The deoximation of a wide range of ketoximes and aldoximes to their corresponding carbonyl compounds with high yields has been achieved using graphene oxide (GO) and sodium nitrite (NaNO2) as highly efficient catalysts and air as the green oxidant under mild conditions. The mechanism of deprotection and recycling use of catalyst were revealed in deep experiment. The carboxylic acid groups on the GO were essential for high catalytic activity. (Figure presented.).
- Tong, Qiaolin,Liu, Yang,Gao, Xuezhi,Fan, Zhanfang,Liu, Tianfu,Li, Bo,Su, Dangsheng,Wang, Qinghe,Cheng, Maosheng
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p. 3137 - 3145
(2019/05/01)
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- Substituent effect study on the experimental 13C NMR chemical shifts of 3-(substituted phenyl)-3a,4,8,8a-tetrahydro-1,3-dioxepino[5,6-d] [1,2] isoxazoles
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Novel heterocyclic derivatives containing isoxazole ring were synthesized by the 1,3-dipolar cycloaddition reaction of substituted nitrile oxides with cis-4,7-dihydro-1,3-dioxepin in the present study. These 3-(substituted phenyl)-3a,4,8,8a-tetrahydro-1,3
- Kara, Yesim S.,Yalduz, Sümeyye
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p. 158 - 165
(2019/05/22)
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- Betulinic acid derivatives: a new class of α-glucosidase inhibitors and LPS-stimulated nitric oxide production inhibition on mouse macrophage RAW 264.7 cells
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Chemical manipulation studies were conducted on betulinic acid (1), twenty-one new rationally designed analogues of 1 with modifications at C-28 were synthesized for their evaluation of inhibitory effects on α-glucosidase and LPS-stimulated nitric oxide production in mouse macrophage RAW 264.7 cells. Compound 2 (IC50 = 5.4 μM) exhibited an almost 1.4-fold increase in α-glucosidase inhibitory activity on yeast α-glucosidase while analogues 5 (IC50 16.4 μM) and 11 (IC50 16.6 μM) exhibited a 2-fold enhanced inhibitory activity on NO-production than betulinic acid.
- Gundoju, Narayanarao,Bokam, Ramesh,Yalavarthi, Nageswara Rao,Azad, Rajaram,Ponnapalli, Mangala Gowri
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supporting information
p. 2618 - 2622
(2018/04/30)
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- Stereospecific 1,4-Metallate Shift Enables Stereoconvergent Synthesis of Ketoximes
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Reported herein is a stereospecific 1,4-metallate rearrangement for single-geometry ketoxime synthesis from oxime chlorides and arylboronic acids. This strategy exhibits broad substrate scope with excellent stereoselectivity under mild reaction conditions. In comparison with the conventional approaches, each configuration of unsymmetric diaryl oximes, as well as the thermodynamically less stable Z isomer of aryl alkyl ketoximes can be selectively and exclusively obtained. The reactivities of unsymmetric diaryl oximes and the Z isomer of aryl alkyl oximes, a class of underexplored molecules, enables efficient access to the corresponding isoquinolines, isoquinoline N-oxides, and amides having a single configuration.
- Yang, Kai,Zhang, Feng,Fang, Tongchang,Zhang, Guan,Song, Qiuling
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supporting information
p. 13421 - 13426
(2019/08/20)
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- Facile one-pot preparation of 5-aryltetrazoles and 3-arylisoxazoles from aryl bromides
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The successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diphenylphosphoryl azide provided efficiently the corresponding 5-aryltetrazoles in good to moderate yields. Similarly, the successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diethyl acetylenedicarboxylate and Oxone provided efficiently the corresponding diethyl 3-arylisoxazole-4,5-dicarboxylates in good to moderate yields. Aromatic aldoximes are the key intermediates in both reactions, and 5-aryltetrazoles and 3-arylisoxazoles could be obtained from aryl bromides in one pot under transition-metal-free conditions.
- Kobayashi, Eiji,Togo, Hideo
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p. 4226 - 4235
(2018/07/06)
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- Synthesis and biological evaluation of novel 1-(aryl-aldehyde-oxime)uracil derivatives as a new class of thymidine phosphorylase inhibitors
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A novel series of 1-(aryl aldehyd oxime) uracil derivatives were synthesized, characterized and evaluated for its inhibitory activity against thymidine phosphorylase. Among them, the compound 8d, 8e, 8f, 8g and 8l displayed potent thymidine phosphorylase
- Zhao, Shuyue,Li, Ke,Jin, Yi,Lin, Jun
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- Novel design of recyclable copper(II) complex supported on magnetic nanoparticles as active catalyst for Beckmann rearrangement in poly(ethylene glycol)
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Copper complex-functionalized magnetic core–shell nanoparticles (Fe3O4@SiO2-Lig-Cu) were prepared and characterized using various techniques. The activity of the new catalyst was tested for the Beckmann rearrangement. The reaction conditions allow for the conversion of a wide variety of aldoximes, including aromatic and heterocyclic ones, to amides in good to excellent yields. High efficiency, mild reaction conditions, easy work-up, use of poly(ethylene glycol) as a green medium and simple purification of products are important advantages of this system. Moreover, the eco-friendly heterogeneous nanocatalyst could be easily recovered from the reaction mixture using an external magnet and reused several times.
- Keyhaniyan, Mahdi,Shiri, Ali,Eshghi, Hossein,Khojastehnezhad, Amir
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- Poly(ethylene glycol)–bound sulfonyl chloride as an efficient catalyst for transformation of aldoximes to nitriles
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An operationally simple, efficient, and environmentally benign preparation of nitriles in good to excellent yields from various aldoximes in the presence of recyclable poly(ethylene glycol)–bound sulfonyl chloride is described.
- Zhang, Xiao-Lan,Liu, Xiao-Ling,Sang, Xiao-Yan,Sheng, Shou-Ri
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p. 232 - 237
(2017/01/22)
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- Synthesis of Tricyclic Isoxazoles via Sequential [3+2] Dipolar Cycloaddition and Palladium-Catalyzed Intramolecular Arylation Reactions
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An efficient synthetic route to tricyclic isoxazoles via sequential copper-catalyzed 1,3-dipolar cycloaddition and palladium-catalyzed intramolecular arylation of isoxazoles is described. Based on these reactions, a convenient one-pot synthesis of the tri
- Guo, Dong-Cai,Zhang, Chao,Li, Fei,Zhang, Fenghua,Yu, Fang,He, Yu-Peng
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p. 1356 - 1370
(2017/03/11)
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- Iron-catalyzed synthesis of benzoxazoles by oxidative coupling/cyclization of phenol derivatives with benzoyl aldehyde oximes
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An iron-catalyzed oxidative coupling/cyclization reaction for the synthesis of benzoxazoles at room temperature is reported. This reaction was enabled by an inexpensive iron(iii) catalyst by treating readily available phenol derivatives with benzoyl aldehyde oximes. Mechanistic studies show that benzoyl aldehyde oxime is not only used as a substrate, but also serves as an ancillary ligand to support the iron salt in the promotion of the transformation.
- Gao, Sen,Gao, Liming,Meng, Hong,Luo, Meiming,Zeng, Xiaoming
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supporting information
p. 9886 - 9889
(2017/09/11)
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- Asymmetric Nitrone Synthesis via Ligand-Enabled Copper-Catalyzed Cope-Type Hydroamination of Cyclopropene with Oxime
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We report realization of the first enantioselective Cope-type hydroamination of oximes for asymmetric nitrone synthesis. The ligand promoted asymmetric cyclopropene "hydronitronylation" process employs a Cu-based catalytic system and readily available starting materials, operates under mild conditions and displays broad scope and exceptionally high enantio- and diastereocontrol. Preliminary mechanistic studies corroborate a CuI-catalytic profile featuring an olefin metalla-retro-Cope aminocupration process as the key C-N bond forming event. This conceptually novel reactivity enables the first example of highly enantioselective catalytic nitrone formation process and will likely spur further developments that may significantly expedite chiral nitrone synthesis.
- Li, Zhanyu,Zhao, Jinbo,Sun, Baozhen,Zhou, Tingting,Liu, Mingzhu,Liu, Shuang,Zhang, Mengru,Zhang, Qian
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supporting information
p. 11702 - 11705
(2017/09/07)
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- NH2OH.HCl/BaCl2: A convenient system for synthesis of oximes from the corresponding of organic carbonyl compounds
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A variety of aldehydes and ketones were converted to their corresponding oximes NH2OH·HCl/BaCl2 system in reflux conditions.
- Talaei, Farhad,Setamdideh, Davood
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p. 1583 - 1587
(2016/08/06)
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- Alkyl Nitrites: Novel Reagents for One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Aldoximes and Alkynes
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An efficient, one-pot approach has been described for the synthesis of 3,5-disubstituted isoxazoles from substituted aldoximes (mixture of E and Z) and alkynes, using alkyl nitrites under conventional heating conditions. The key nitrile oxide intermediates that are required for the synthesis of isoxazoles are formed by treatment of substituted aldoxime with either tert-butyl nitrite or isoamyl nitrite. The generated nitrile oxides underwent in situ [3+2] dipolar cycloaddition to the substituted alkynes to give 3,5-disubstituted isoxazoles regioselectively in high to excellent yields. The developed synthetic methodology was applied for the synthesis of a previously reported potent hDGAT1 inhibitor.
- Kadam, Kishorkumar S.,Gandhi, Thirumanavelan,Gupte, Amol,Gangopadhyay,Sharma, Rajiv
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p. 3996 - 4008
(2016/11/11)
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- (Thiolan-2-yl)diphenylmethyl benzyl ether/N,N′-diarylurea cocatalyzed asymmetric aziridination of cinnamyl bromide and aryl aldimine
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A dual catalyst system using THT-based chiral sulfide 2a and H-bond donor 10a was developed for the asymmetric imino Corey-Chaykovsky reaction. Under the optimum reaction conditions, cinnamyl bromide reacted with a wide scope of N-diphenylphosphinic aldim
- Wang, Shang-Hua,Chein, Rong-Jie
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supporting information
p. 2607 - 2615
(2016/05/11)
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- APPLICATIONS OF N6-SUBSTITUTED ADENOSINE DERIVATIVE AND N6-SUBSTITUTED ADENINE DERIVATIVE TO CALMING, HYPNOSES, CONVULSION RESISTANCE, EPILEPTIC RESISTANCE, PARKINSON DISEASE RESISTANCE, AND DEMENTIA PREVENTION AND TREATMENT
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PROBLEM TO BE SOLVED: To prepare analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. SOLUTION: The present invention relates to an N6-substituted adenosine derivative and an N6-substituted adenine derivative selected from the group consisting of specific compounds. The present invention also relates to a pharmaceutical composition at least comprising a therapeutically effective amount of the compounds and a pharmaceutically acceptable carrier. The invention further relates to the compounds used in preparation of analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. COPYRIGHT: (C)2016,JPO&INPIT
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Paragraph 0097
(2018/10/27)
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- An eco-friendly system for oximation of organic carbonyl compounds under microwave irradiation
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The oximation of a variety of organic carbonyl compounds was efficiently carried out with NH2OH?HCl under microwave irradiation. The reactions were performed in water or water-ethanol as green solvents to give Z-aldoxime isomers from the corresponding aldehydes and E-ketoxime isomers from the corresponding ketones in a perfect selectively with excellent yields.
- Batmani, Hana,Setamdideh, Davood
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p. 699 - 703
(2015/01/16)
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- POLYCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING THE SAME
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The present disclosure provides compounds, or pharmaceutically acceptable salts thereof, for inhibiting the growth of a microbe; treating a mammal having a microbial infection, malaria, mucositis, an ophthalmic infection, an otic infection, a cancer, or a Mycobacterium infection; killing or inhibiting the growth of a Plasmodium species; inhibiting the growth of a Mycobacterium species; modulating an immune response in a mammal; or antagonizing unfractionated heparin, low molecular weight heparin, or a heparin/low molecular weight heparin derivative.
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Page/Page column 166
(2014/07/07)
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- Enantioselective synthesis of diaryl aziridines using tetrahydrothiophene- based chiral sulfides as organocatalysts
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This work describes catalytic and asymmetric aziridinations (15 examples, 95-98% ee) of benzyl bromide and imines via the imino Corey-Chaykovsky reaction using (thiolan-2-yl)diarylmethanol benzyl ether as an organocatalyst. The catalyst and analogues thereof were prepared through an expeditious and efficient synthetic route featuring a double nucleophilic substitution and Shi epoxidation as key steps.
- Huang, Meng-Ting,Wu, Hsin-Yi,Chein, Rong-Jie
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supporting information
p. 1101 - 1103
(2014/01/17)
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- Organocatalytic, diastereo- and enantioselective synthesis of nonsymmetric cis -stilbene diamines: A platform for the preparation of single-enantiomer cis -imidazolines for protein-protein inhibition
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The finding by scientists at Hoffmann-La Roche that cis-imidazolines could disrupt the protein-protein interaction between p53 and MDM2, thereby inducing apoptosis in cancer cells, raised considerable interest in this scaffold over the past decade. Initial routes to these small molecules (i.e., Nutlin-3) provided only the racemic form, with enantiomers being enriched by chromatographic separation using high-pressure liquid chromatography (HPLC) and a chiral stationary phase. Reported here is the first application of an enantioselective aza-Henry approach to nonsymmetric cis-stilbene diamines and cis-imidazolines. Two novel mono(amidine) organocatalysts (MAM) were discovered to provide high levels of enantioselection (>95% ee) across a broad range of substrate combinations. Furthermore, the versatility of the aza-Henry strategy for preparing nonsymmetric cis-imidazolines is illustrated by a comparison of the roles of aryl nitromethane and aryl aldimine in the key step, which revealed unique substrate electronic effects providing direction for aza-Henry substrate-catalyst matching. This method was used to prepare highly substituted cis-4,5-diaryl imidazolines that project unique aromatic rings, and these were evaluated for MDM2-p53 inhibition in a fluorescence polarization assay. The diversification of access to cis-stilbene diamine-derived imidazolines provided by this platform should streamline their further development as chemical tools for disrupting protein-protein interactions.
- Vara, Brandon A.,Mayasundari, Anand,Tellis, John C.,Danneman, Michael W.,Arredondo, Vanessa,Davis, Tyler A.,Min, Jaeki,Finch, Kristin,Guy, R. Kiplin,Johnston, Jeffrey N.
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p. 6913 - 6938
(2014/08/18)
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- N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
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Paragraph 0096
(2013/03/26)
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- Highly selective and efficient lewis acid-base catalysts based on lanthanide-containing polyoxometalates for oximation of aldehydes and ketones
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Two lanthanide-containing polyoxometalates (POMs) have been developed as Lewis acid-base catalysts for highly selective and efficient oximation of various aldehydes and ketones under mild conditions. Copyright
- Zhao, Shen,Huang, Lujiang,Song, Yu-Fei
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p. 1659 - 1663
(2013/05/09)
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- Synthesis of oximes with NH2OH.HCl/DOWEX(R)50WX4 system
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The oximation of a variety of carbonyl compounds was efficiently carried out with DOWEX(R)50WX4/NH2OH·HCl system. The reactions were performed in ethanol to give Z-aldoximation isomers of aldehydes and E-oximaton of acetophenone derivatives in a perfect selectively. The oximation of compounds with two carbonyl groups was carried out selectively on one carbonyl moiety. Also, the oximation of aldehydes over ketones has been accomplished successfully by this system.
- Setamdideh, Davood,Khezri, Behrooz,Esmaeilzadeh, Seyran
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p. 1119 - 1124
(2012/10/30)
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- Ruthenium-catalyzed rearrangement of aldoximes to primary amides in water
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The rearrangement of aldoximes to primary amides has been studied using the readily available arene-ruthenium(II) complex [RuCl2(η 6-C6Me6){P(NMe2)3}] (5 mol %) as catalyst. Reactions proceeded cleanly in pure water at 100 °C without the assistance of any cocatalyst, affording the desired amides in high yields (70-90%) after short reaction times (1-7 h). The process was operative with both aromatic, heteroaromatic, α,β-unsaturated, and aliphatic aldoximes and tolerated several functional groups. Reaction profiles and experiments using 18O-labeled water indicate that two different mechanisms are implicated in these transformations. In both of them, nitrile intermediates are initially formed by dehydration of the aldoximes. These intermediates are then hydrated to the corresponding amides by the action of a second molecule of aldoxime or water. A kinetic analysis of the rearrangement of benzaldoxime to benzamide is also discussed.
- Garcia-Alvarez, Rocio,Diaz-Alvarez, Alba E.,Borge, Javier,Crochet, Pascale,Cadierno, Victorio
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p. 6482 - 6490
(2012/10/30)
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- Synthesis, characterization and biological evaluation of some novel 17-isoxazoles in the estrone series
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Regioselective 1,3-dipolar cycloadditions of different aryl nitrile oxides to mestranol were carried out to furnish novel steroidal 17α-isoxazoles in good to excellent yields. Copper(I) was found to be an efficient catalyst, accelerating the intermolecula
- Kovacs, Dora,Kadar, Zalan,Motyan, Gerg,Schneider, Gyula,Woelfling, Janos,Zupko, Istvan,Frank, Eva
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p. 1075 - 1085
(2012/11/07)
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- Efficient synthesis of oxazoles by dirhodium(ii)-catalyzed reactions of styryl diazoacetate with oximes
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An efficient one-step synthesis of multi-functionalized oxazole derivatives is achieved in high yield by dirhodium(ii)-catalyzed reactions of styryl diazoacetate with aryl oximes. This journal is
- Xu, Xinfang,Zavalij, Peter Y.,Doyle, Michael P.,Hu, Wenhao
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supporting information
p. 11522 - 11524,3
(2012/12/12)
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- N6-SUBSTITUTED ADENOSINE DERIVATIVES, N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
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Page/Page column 39-40
(2012/11/06)
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- Selective synthesis of E-isomers of aldoximes via a domino aza-Michael/retro-Michael reaction
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A highly stereoselective synthesis of E-isomer of aldoximes was developed through a basecatalysed domino aza-Michael/retro-Michael reaction of hydroxylamine and 2-(R-benzylidene)malononitrile. This reaction generates (E)-aldoxime diastereomer in high yields (eight examples, isolated yields of 82-93 %), excellent diastereomeric purity (diastereomeric ratio higher than 95 : 5 by 1H NMR), and proceeds under mild reaction conditions (aqueous NaOH, pH 12, room temperature, 4 h).
- Chen, Wei,Yu, Wei-Guo,Shi, Hai-Bo,Lu, Xiao-Yan
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experimental part
p. 308 - 311
(2012/08/28)
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- Selective synthesis of E-isomers of aldoximes via a domino aza-Michael/retro-Michael reaction
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A highly stereoselective synthesis of E-isomer of aldoximes was developed through a base-catalysed domino aza-Michael/retro-Michael reaction of hydroxylamine and 2-(R-benzylidene)malononitrile. This reaction generates (E)-aldoxime diastereomer in high yie
- Chen, Wei,Yu, Wei-Guo,Shi, Hai-Bo,Lu, Xiao-Yan
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p. 308 - 311
(2015/03/04)
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- Unexpected C-C bond cleavage: Synthesis of 1,2,4-oxadiazol-5-ones from amidoximes with pentafluorophenyl or trifluoromethyl anion acting as leaving group
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An unexpected C-C bond cleavage has been observed on pentafluorobenzoylamidoximes under mild basic conditions. This observation has been exploited to develop a new synthesis of 1,2,4-oxadiazol-5-ones from amidoximes using pentafluorobenzoyl chloride or trifluoroacetic anhydride (TFAA) as a double acylating agent. The pentafluorophenyl anion and the trifluoromethyl anion acted as leaving groups in this transformation.
- Gerfaud, Thibaud,Wei, Hai-Long,Neuville, Luc,Zhu, Jieping
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supporting information; experimental part
p. 6172 - 6175
(2012/01/03)
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- AlPW12O40 and AlPMo12O40 as highly effective and eco-friendly catalysts for aldoximation of aldehydes under solvent-free conditions
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The oxime formation of aromatic aldehydes has directly been carried out with hydroxylamine hydrochloride using heteropoly acids (AlPW12O 40, AlPMo12O40) as catalysts in the absence of solvent. It is found that these heteropoly acids were effective catalysts for the formation of oxime of aldehydes. This method consistently has the advantage of high yields of the products, short reaction time, mild and solvent-free conditions, cleaner reactions and isolation procedures.
- Fazaeli, Razieh,Aliyan, Hamid
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experimental part
p. 855 - 858
(2012/04/04)
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- O-acetyl oximes as transformable directing groups for Pd-catalyzed C-H bond functionalization
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[Chemical equation presented] O-Acetyl oxlmes serve as effective directing groups for Pd-catalyzed sp2 and sp3 C-H functionalization reactions. The C-H functionalization products can be subsequently transformed Into ortho- or β-functionalized ketones, alcohols, amines, and heterocycles.
- Neufeldt, Sharon R.,Sanford, Melanie S.
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supporting information; experimental part
p. 532 - 535
(2010/05/02)
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- ISOXAZOLE-PYRIDINE DERIVATIVES
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The present invention is concerned with isoxazole-pyridine derivatives of formula I wherein X, R1 to R6 are as described herein. The compounds are active on the GABA A α5 receptor binding site and useful for the treatment of cognitive disorders, such as Alzheimer's disease.
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Page/Page column 53
(2009/06/27)
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- Novel oxidative nitrogen to carbon rearrangement found in the conversion of anilines to benzaldoximes by treating with HCHO/H2O2
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Novel rearrangement was found by reacting anilines with HCHO/H2O2 resulting in the synthesis of various benzaldoximes. The mechanism of the rearrangement is proposed and suggested that the rearrangement might proceed via unstable N-phenyloxazirane intermediate followed by the transfer of aryl moiety from nitrogen to carbon atom leading to the formation of benzaldoxime.
- Kapuriya, Naval,Kapuriya, Kalpana,Dodia, Narsinh M.,Lin, Yi-Wen,Kakadiya, Rajesh,Wu, Chao-Ting,Chen, Ching-Huang,Naliapara, Yogesh,Su, Tsann-Long
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p. 2886 - 2890
(2008/09/21)
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- Biologically active hydroxymoyl chlorides as antifungal agents
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Several oximes and oxime ethers have been developed as antimicrobial agents. A series of chlorooximes (hydroximoyl chlorides) have been synthesized and tested for antifungal activity under in-vitro conditions against Candida albicans, Candida parapsilosis, Candida glabrata, Candida krusei, Aspergillus fumigatus, Aspergilhis flaviis and Aspergillus niger. The derived antifungal activity has been compared with the corresponding oximes. The results show that most of the chlorooximes exhibit potent antifungal activity with anti-isomers showing better activity. It is observed that most of the chlorooximes show interesting antifungal activity (MICs ≤ 32 μg/mL) compared to oximes. Compound 3q (2,3-dimethoxy phenyl hydroxymoyl chloride) is the most active compound. This compound is active against all the Candida species (MIC 0.5 μg/mL) as well as filamentous fungi with MIC range of 2-4 μg/mL. This series of compounds are fungicidal in nature as evident from the MFC results.
- Ismail, Tabasum,Shafi, Syed,Singh, Parvinder Pal,Qazi, Naveed Ahmed,Sawant, Sanghapal D.,Ali, Intzar,Khan, Inshad Ali,Kumar,Qazi, Ghulam Nabi,Alam, M. Sarwar
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p. 740 - 747
(2008/12/20)
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