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A series of novel IMB-070593 derivatives containing a substituted benzyloxime moiety and displaying a remarkable improvement in lipophilicity were synthesized and evaluated for their in vitro antimycobacterial and antibacterial activity. Our results reveal that the target compounds 19a-m have considerable Gram-positive activity (MIC: <0.008-32 mug/mL), although they are generally less active than the reference drugs against the Gram-negative strains. In particular, compounds 19h, 19j, 19k and 19m show good activity (MICs: <0.008-4 mug/mL) against all of the tested Gram-positive strains, including ciprofloxacin (CPFX)- and/or levofloxacin (LVFX)-resistant MSSA, MRSA and MSSE. Moreover, compound 19l (MIC: 0.125 mug/mL) is found to be 2-4 fold more active than the parent IMB070593, CPFX and LVFX against M. tuberculosis H37Rv ATCC 27294. The catalyzed pathway has a lower Ea, but the net change in energy that results from the reaction is not affected by the presence of a catalyst. In my other articles, you can also check out more blogs about 39270-39-8 Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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We describe the enantiomeric and enantiotopic analysis of the NMR spectra of compounds derived from the functionalized cone-shaped core, cyclotriveratrylenes (CTV), dissolved in weakly oriented lyotropic chiral liquid crystals (CLCs) based on organic solutions of poly-gamma-benzyl-L-glutamate. The CTV core lacks prostereogenic as well as stereogenic tetrahedral centers. However, depending on the pattern of substitution, chiral and achiral compounds with different symmetries can be obtained. Thus, symmetrically nonasubstituted CTVs (C3 symmetry) are optically active and exhibit enantiomeric isomers, while symmetrically hexasubstituted (C3v symmetry) derivatives are prochiral and possess enantiotopic elements. In the first part we use 2H and 13C NMR to study two nonasubstituted (-OH or -OCH3) CTVs, where the ring methylenes are fully deuterated, and show for the first time that the observation of enantiomeric discrimination of chiral molecules with a 3-fold symmetry axis is possible in a CLC. It is argued that this discrimination reflects different orientational ordering of the M and P isomers, rather than specific chiral short-range solvent-solute interactions that may affect differently the magnetic parameters of the enantiomers or even their geometry. In the second part we present similar measurements on hexasubstituted CTV with flexible side groups (-OC(O)CH3 and the, partially deuterated bidentate, -OCH2CH2O-), having on the average C3v symmetry. No spectral discrimination of enantiotopic sites was detected for the -OC(O)CH3 derivative. This is consistent with a recent theoretical work (J. Chem. Phys. 1999, 111, 6890) that indicates that in C3v molecules no chiral discrimination between enantiotopic elements, based on ordering, is possible. In contrast, a clear splitting was observed in the 2H spectra of the enantiotopic deuterons of the side groups in the tri(dioxyethylene)-CTV. It is argued that this discrimination reflects different ordering characteristics of the various, rapidly (on the NMR time scale) interconverting conformers of this compound. Assuming two twisted structures for each of the dioxyethylene side groups, four different conformers are expected, comprising two sets of enantiomeric pairs with, respectively, C3 and C1 symmetries. Differential ordering and/or fractional population imbalance of these enantiomeric pairs leads to the observed spectral discrimination of sites in the side chains that on average form enantiotopic pairs.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Gaucher disease is a lysosomal storage disorder (LSD) caused by deficiency in the enzyme glucocerebrosidase (GC). Small molecule chaperones of protein folding and translocation have been proposed as a promising therapeutic approach to this LSD. Most small molecule chaperones described in the literature contain an iminosugar scaffold. Here we present the discovery and evaluation of a new series of GC inhibitors with a quinazoline core. We demonstrate that this series can improve the translocation of GC to the lysosome in patient-derived cells. To optimize this chemical series, systematic synthetic modifications were performed and the SAR was evaluated and compared using three different readouts of compound activity: enzymatic inhibition, enzyme thermostabilization, and lysosomal translocation of GC.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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We describe an eco-friendly, practical and operationally simple procedure for the bis(methoxypropyl) ether-promoted oxidation of aromatic alcohols into aromatic carboxylic acids and aromatic ketones with atmospheric dioxygen as the sole oxidant. This chemical process is clean with high conversion and good selectivity, and an external initiator, catalyst, additive and base are not required. The virtue of this reaction is highlighted by its easily available and economical raw materials and excellent functional group tolerance (acid-, base- and oxidant-labile groups).

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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A cyclometalated rhodium complex has been shown to perform highly selective and efficient reduction of aldehydes, deriving the hydrogen from methanol. With methanol as both the solvent and hydrogen donor under mild conditions and an open atmosphere, a wide range of aromatic aldehydes were reduced to the corresponding alcohols, without affecting other functional groups.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Propynyl benzyl ethers having juvenile hormone-like activity which are 4-halogen, lower alkyl, lower alkoxy or propynyloxy substituted or 3,4-lower alkylenedioxy substituted and which can also be 3,5- and/or alpha-substituted, and insecticide compositions that include at least one propynyl benzyl ether and that can also include a conventional insect-poison.

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Benzodioxan,
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Cyclohexane and cyclohexene derivatives and pharmaceutically acceptable derivatives hereof useful in methods of treatment of bacterial infections in mammals, particularly man.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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A palladium-catalyzed reaction of methylenespiropentane (11) with iodobenzene (12) under typical Heck conditions [Pd(OAc)2, PPh 3, Et3N, DMF] produced a mixture of the unstable [3]dendralene 13 and allylidenecyclopropane 14 in 38 % yield. When an analogous reaction with iodobenzene was carried out in the presence of morpholine (25) and of tris(2-furyl)phosphane (TFP) instead of triphenylphosphane, the dienes 26, 28 and 31 were generated by nucleophilic trapping of pi-allylpalladium intermediates 30 and 32. The cross coupling of methylenespiropentane (11) with the functionalized aryl iodides 33a-g in the presence of a palladium precatalyst [Pd(OAc)2, TFP, Et3N, DMF] at 80C, 3 h, provided the seven-membered 3,4-dimethylene-substituted heterocycles 34a-g and 35b which, upon addition of dimethyl fumarate (19), underwent Diels-Alder reactions to furnish bicyclic and higher oligocyclic dihydrobenzoxepine and -benzazepine derivatives 36a-g and 37b, yet in rather moderate yields of 18-29% only. The overall process constitutes a one-pot, two-step, three-component queuing cascade. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Compounds of formula (I’) wherein A, R1, R2, T1, T2, T3, T4, L, W, Z, R”’, m and n have the meaning according to the claims can be employed, inter alia, for the treatment of tauopathies and Alzheimer’s disease.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Oleuropein is a glucosylated seco-iridoid present in olive fruits and leaves. Due to its broad spectrum of biological activities, including anticancer properties, oleuropein has attracted scientific attention for the past 20 years. The promising antiproliferative activity of an olive leaf extract enriched in oleuropein against a series of human cancer cell lines, prompted us to proceed with the semi-synthesis of 51 analogs of oleuropein. Following their initial screening against the estrogen receptor negative breast cancer cell line SKBR3, 7 analogs were shown to display significant cytotoxicity and were further tested against 6 additional solid tumor-derived and leukemic cell lines. The analog with the most promising antitumor activity (24) was selected for more detailed studies. 24 was non-toxic to peripheral blood mononuclear cells derived from healthy blood donors when tested at concentrations close to its half maximal inhibitory concentration. In vivo administration of 24 in melanoma-bearing mice resulted in reducing tumor size in a dose-dependent manner and in inducing anti-melanoma-reactive immune responses. Our results suggest that analog 24, emerging from the initial structure of oleuropein, represents a promising lead structure for further optimization.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem