- A Ball-Milling-Enabled Cross-Electrophile Coupling
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The nickel-catalyzed cross-electrophile coupling of aryl halides and alkyl halides enabled by ball-milling is herein described. Under a mechanochemical manifold, the reductive C-C bond formation was achieved in the absence of bulk solvent and air/moisture sensitive setups, in reaction times of 2 h. The mechanical action provided by ball milling permits the use of a range of zinc sources to turnover the nickel catalytic cycle, enabling the synthesis of 28 cross-electrophile coupled products.
- Jones, Andrew C.,Nicholson, William I.,Leitch, Jamie A.,Browne, Duncan L.
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supporting information
p. 6337 - 6341
(2021/08/23)
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- Terminal-Selective C(sp3)-H Arylation: NiH-Catalyzed Remote Hydroarylation of Unactivated Internal Olefins
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A terminal-selective migratory hydroarylation of unactivated olefins has been developed though a NiH-catalyzed alkene isomerization-hydroarylation relay process. This sp3C-H arylation was achieved with a simple pyrox ligand under mild conditions. The practicality and synthetic flexibility of the method is highlighted by the successful regioconvergent conversion of isomeric mixtures of alkenes to value-added linear arylation products on a gram scale.
- He, Yuli,Han, Bo,Zhu, Shaolin
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supporting information
p. 2253 - 2264
(2021/05/05)
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- RATIONALLY DESIGNED LAWSONE DERIVATIVES AS ANTIMICROBIALS AGAINST MULTIDRUG-RESISTANT STAPHYLOCOCCUS AUREUS
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Naphthoquinone derivatives of Lawsone have been found to be effective against Staphylococcus aureus and methicillin-resistant Staphylococcus aureus (MRSA). Such compounds generally contain a substituent group at the 3-position of a specific naphthoquinone compound, i.e. 2-hydroxy-1,4-naphthoquinone. One of these derivatives referred to as compound 6c in the series exhibits potent antimicrobial activity that is comparable to that of the two commercial antibiotics ofloxacin and ciprofloxacin against the two strains of methicillin sensitive Staphylococcus aureus (MSSA; ATCC 29213 and ATCC 6538). In the case of two strains of MRSA (ATCC BAA-44 and ATCC BAA-1717) that have developed drug resistance to both ofloxacin and ciprofloxacin, the antimicrobial activity of 6c can almost rival that of vancomycin and daptomycin. Furthermore, 6c is also effective against vancomycin-intermediate and daptomycin non-susceptible strain of MRSA (ATCC 700699). Besides the efficacy, 6c has a much improved drug resistance profile in comparison with the conventional antibiotics.
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Paragraph 0029-0030; 0033
(2021/03/05)
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- Antimycobacterial activity evaluation, time-kill kinetic and 3D-QSAR study of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives
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A series of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives were synthesized and evaluated for their antitubercular activity. Some of the compounds exhibited potent activity against Mycobacterium tuberculosis H37Rv. One of the compound having t-butyl at para position of the benzene ring showed excellent activity even better than the standard drug ethambutol with MIC value 1.1 ± 0.2 μM. The time-kill kinetics study of two most active compounds showed rapid killing of the M. tuberculosis within 4 days. Additionally atom-based quantitative structure-activity relationship (QSAR) model was developed that gave a statistically satisfying result (R2) = 0.92, Q2 = 0.75, Pearson-R = 0.96 and effectively predicts the anti-tuberculosis activity of training and test set compounds.
- Kumar, Deepak,Raj, K. Kranthi,Bailey, Maiann,Alling, Torey,Parish, Tanya,Rawat, Diwan S.
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p. 1365 - 1369
(2013/03/14)
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- Synthesis and characterization of π-extended porphyrins as potential precursors for the formation of columnar mesophases: Design principles for columnar mesophases need revision?
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A series of meso-a bridged extended porphyrins substituted with long aliphatic chains were synthesized and fully characterized. Two different synthetic strategies were tested to obtain the target structures. The synthetic steps were optimized in order to obtain scalable routes for the production of sufficient quantities of η-extended porphyrins for material science studies. The porphyrins were obtained either as free bases or complexed with Ni II or CuII. UV-Vis spectroscopy and polarized light microscopy was used for the analysis of the material properties of the η-extended porphyrins. The results obtained with our compounds are not compatible with the results reported in the literature. ARKAT-USA, Inc.
- Herzog, Beat,Neier, Reinhard
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- S1P RECEPTORS MODULATORS AND THEIR USE THEREOF
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The invention relates to novel compounds that have S1P receptor modulating activity. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, autoimmune response. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as autoimmune response.
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Page/Page column 48-49
(2010/04/30)
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- S1P RECEPTORS MODULATORS
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The invention relates to novel compounds that have S1P receptor modulating activity and, preferably, apoptotic activity and/or anti proliferative activity against cancer cells and other cell types. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, cancer. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as cancer.
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Page/Page column 87
(2010/04/30)
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- COMPOSITIONS AND METHODS FOR INHIBITING SPHINGOSINE KINASE
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Amidine analogs that can inhibit the activity of sphingosine kinase 1 and sphingosine kinase 2 (SphK1 and SphK2) are provided. The compounds can prevent angiogenesis in tumor cells.
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Page/Page column 31; 32
(2009/12/27)
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- Molecular recognition of viologen by zinc porphyrinic receptors with diarylurea sidearms. Toward construction of a supramolecular electron transfer system
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A series of zinc porphyrinic receptors for a viologen substrate (hexyl viologen, HV2+) were synthesized, in which varying numbers of diarylurea moieties, from one to four, were appended at the porphyrin's meso positions. The increase in the number of the diarylurea moiety led to the increase in stability of the receptor-HV2+ complex, showing that the convergent dipoles set up on the porphyrin platform played an essential role in the complexation. In this system, formation of the stable electron donor-acceptor complex resulted in the effective electron transfer from the singlet excited state of the zinc porphyrin to HV2+.
- Ezoe, Masayuki,Yagi, Shigeyuki,Nakazumi, Hiroyuki,Itou, Mitsunari,Araki, Yasuyuki,Ito, Osamu
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p. 2501 - 2510
(2007/10/03)
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- Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids
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Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides and chlorides undergoes Suzuki cross-coupling with alkylboronic acids in good yields. Several alkyl substituents such as ethyl, n-butyl, n-octyl, isobutyl or 2,2-dimethylpropyl on the alkylboronic acids have been successfully used. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides.
- Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
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p. 3813 - 3818
(2007/10/03)
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- Preparation of substituted aromatic compounds
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A process for preparing compounds of the formula (II), where the substituents R1 to R5 are each independently H, CH3, straight-chain or branched C1-C8-alkyl, CH(OC1-C5-alkyl)2, CH(C1-C5-alkyl)(OC1-C5-alkyl), CH2(OC1-C5-alkyl), CH(CH3)(OC1-C5-alkyl), C1-C8-alkoxy, N(C1-C5-alkyl)2, phenyl, substituted phenyl, aryl, heteroaryl, S(C1-C5-alkyl) or a radical Caryl, alkyl, and the symbols X1 to 5 are each carbon or a maximum of two neighboring X1-5 are nitrogen or X1R1 and X2R2 together are O, NH, N(C1-C5-alkyl), N(C═O—C1-C5-alkyl), N(SiR3)2 or S, or where neighboring radicals R1 to R5 form the following structural unit, where X6 to X9 and R6 to R9 have the same meaning as X1 to X5 and R1 to R5 which comprises reacting chloro- or fluoroaromatics of the formula (I) with carbon electrophiles and lithium metal.
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- Synthesis of 2-nitroalcohols by regioselective ring opening of epoxides with MgSO4/MeOH/NaNO2 system: A short synthesis of immunosuppressive agent FTY-720
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It has been demonstrated that a variety of epoxides can easily be opened with a system consisting of MgSO4/MeOH/NaNO2 giving the corresponding 2-nitroalcohols in excellent yields. This strategy has been applied to achieve a short synthesis of Immunosuppressive Agent FTY - 720.
- Kalita,Barua,Bezbarua,Bez
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p. 1411 - 1414
(2007/10/03)
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- Synthesis of p-Alkyl-, p-Alkoxy-, and p-Acyloxycinnamates with trans-4-Phenylcyclohexyl and 4-Biphenylyl Fragments and Their Mesomorphic Properties
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Acylation of trans-4-phenylcyclohexanol and p-cyano-p'-hydroxybiphenyl with p-n-alkyl-, p-n-alkoxy-, and p-n-alkanoyloxycinnamoyl chlorides yields corresponding cinnamates.
- Bykova, V. V.,Zharova, M. A.,Maidachenko, G. G.
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p. 1143 - 1145
(2007/10/03)
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- Photochemical behavior of micellized 4-(4′-alkylstyryl)pyridinium salts
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New photochromic surfactants, l-alkyl-4-(4′-alkylstyryl)lpyridinium halides (CnStzRX; n = 0, 4, 6, 8; R = Me, Et, CH2CH2OH, n-Bu, n-C9H19; X = Br, I), were synthesized and the photochemical behavior of their micellar aggregates in water was characterized in relation to non-micellizing l-methyl-4-stilbazolium ions. Reversible trans-cis isomerization through a photothermal cycle was observed for the micellized CnStzRX. Furthermore, photoreactions upon prolonged irradiation of CnStzRX micelles resulted in a 3-31% formation of thermodynamically least stable syn-head-to-head and ca. 3% of anti- head-to-head dimers. These findings indicate that the self aggregation process of CnStzRX may provide some topologically organized microenvironment affecting the steric and like-charge repulsions of the aggregate components.
- Kozlecki, Tomasz,Wilk, Kazimiera A.
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p. 645 - 651
(2007/10/03)
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- New potent antagonists of leukotrienes C4 and D4. 1. Synthesis and structure-activity relationships
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(p-Amylcinnamoyl)anthranilic acid (3a) had moderate antagonist activities against LTD4-induced smooth muscle contraction on guinea pig ileum and LTC4-induced bronchoconstriction in anesthetized guinea pigs. Modifications were made in the hydrophobic part (cinnamoyl moiety) and the hydrophilic part (anthranilate moiety) of 3a. A series of 8-(benzoylamino)-2-tetrazol-5-yl-1,4-benzodioxans and 8-(benzoylamino)-2-tetrazol-5-yl-4-oxo-4H-1-benzopyrans were revealed to be potent antagonists of leukotrienes C4 and D4. Among both series, ONO-RS-347 (18k) and ONO-RS411 (19h) were the most potent and orally active antagonists, respectively. Structure-activity relationships are discussed.
- Nakai,Konno,Kosuge,Sakuyama,Toda,Arai,Obata,Katsube,Miyamoto,Okegawa,Kawasaki
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- Synthesis of Unbranched 4-Alkylbenzaldehydes
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The preparation of unbranched 4-alkylbenzaldehydes free of positional and branched-chain isomers by different methods is described.A one-step preparation of the aldehydes is reported which involves the direct hydrogenation of a Friedel-Craft's complex in the presence of Pd/C catalyst.
- Osman, Maged A.
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p. 2448 - 2449
(2007/10/02)
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- LOW-MELTING NEMATIC 4,4 prime -BIS-(ALKYLBENZAL)-2-CHLORO-1,4-PHENYLENEDIAMINES.
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A series of 4,4 prime -bis(alkylbenzal)-2-chloro-1,4-phenylenediamines were prepared and their mesomorphic behavior characterized. All homologues showed nematic behavior with broad mesophases and rather low-melting points. The mesomorphic behavior is compared with that obtained from the 4,4 prime -bis-(alkoxybenzal)-1,4-phenylenediamine series and the 4,4 prime -bis-(alkoxybenzal)-2-chloro-1,4-phenylenediamine series.
- Cole,Sowa
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p. 149 - 153,150, 151
(2007/10/09)
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