The Shocking Revelation of C8H9NO2

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A process of providing novel compounds of Formula (I) below, which are useful as intermediates in the preparation of camptothecin and camptothecin-like compounds, STR1 wherein: R1 represents alkyl, particularly methyl, R2 represents H or alkyl, particularly methyl, R3 represents H or alkyl, particularly H; Q represents triflate or halo particularly bromo and iodo more particularly iodo and Y represents H, chloro or OR4, wherein R4 represents alkyl or triflate, or particularly H.

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

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The synthesis, characterization and catalytic activity of a Cu(II) complex derived from 2-oxoquinoline-3-carbaldehyde Schiff base supported on amino-functionalized silica are reported. 3-(1H-Benzo[d]imidazol-2-yl)quinolines containing piperidine, morpholine and phenylpiperazine skeletons at the C-2 position were formed in good to excellent yields via the one-pot reaction of 2-chloroquinoline-3-carbaldehyde, benzene-1,2-diamines and secondary amines in the presence of the nanocatalyst under mild conditions. Moreover, the nanocatalyst was found to be recyclable for up to seven runs without significant loss of activity. Also, a series of 2H-indazoles were synthesized by the catalytic condensation of 2-bromobenzaldehyde, sodium azide and primary amines.

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

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Homocamptothecins (hCPTs) represent a class of new emerging antitumor agents, which contains a seven-membered beta-hydroxylactone in place of the conventional six-membered alpha-hydroxylactone ring (E ring) of camptothecins. Some novel 7-substituted hCPTs were designed and synthesized based on a newly developed synthetic route which couples ring A with ring C, E and D. Most of the synthesized compounds exhibit very high cytotoxic activity on tumor cell line A549. Some compounds, such as 9b, 9l, and 9y, show broad in vitro antitumor spectrum and are more potent than topotecan. Three-dimensional quantitative structure-activity relationship (3D-QSAR) methods, CoMFA and CoMSIA, were applied to explain the structure-activity relationship (SAR) of the synthesized compounds. Furthermore, molecular docking was used to clarify the binding mode of the synthesized compounds to human DNA topoisomerase I. The important hydrophobic, base-pair stacking, and hydrogen-bonding interactions were observed between the hCPT derivatives and their receptor. The results from molecular modeling will guide the design of novel hCPTs with higher antitumor activity.

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

The Shocking Revelation of 2,3-Dihydrobenzo[b][1,4]dioxin-6-amine

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A gold-catalyzed post-Ugi cascade transformation for the synthesis of 2-pyridones is described. The process involves furan?alkyne cyclization followed by furan ring-opening and cleavage of the isocyanide-originated fragment. The initially formed cis double bond can isomerize into a more stable trans double bond upon prolonged exposure to a strong Br°nsted acid. Thus, the overall strategy provides a viable access towards two types of 2-pyridones.

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

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The inhibition of human glutaminyl cyclase (hQC) has come into focus as a new potential approach for the treatment of Alzheimer’s disease. The hallmark of this principle is the prevention of the formation of Abeta 3,11(pE)-40,42, as these Abeta-species were shown to be of elevated neurotoxicity and likely to act as a seeding core leading to an accelerated formation of Abeta-oligomers and fibrils. Starting from 1-(3-(1H-imidazol-1- yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea, bioisosteric replacements led to the development of new classes of inhibitors. The optimization of the metal-binding group was achieved by homology modeling and afforded a first insight into the probable binding mode of the inhibitors in the hQC active site. The efficacy assessment of the hQC inhibitors was performed in cell culture, directly monitoring the inhibition of Abeta3,11(pE)-40,42 formation. 2009 American Chemical Society.

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

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The present research work involved the reaction of 2,3-dihydro-1,4-benzodioxin-6-amine (1) and benzenesulfonyl chloride (2) under dynamic pH control at 10 using aqueous Na2CO3. This reaction yielded 2,3-dihydro-1,4-benzodioxin-6-yl)benzenesulfonamide (3), which was further substituted at N-position with various alkyl/aryl halides (4a ? 4m) in N,N-dimethylformamide and catalytic amount of lithium hydride to obtain N-substituted (2,3-dihydro-1,4-benzodioxin-6-yl)benzenesulfonamides (5a ? 5m). The projected structures of the synthesized derivatives were confirmed using various spectral techniques (IR,1H NMR and EIMS). The synthesized derivatives were screened for antibacterial potential and inhibitory activity against lipoxygenase enzyme.

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

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In a search for therapeutic agents for the treatment of osteoporosis and bone fracture, we found that 2-benzothiopyran-1-carboxamide derivatives 1, derived from ipriflavone as a lead compound, increase cellular alkaline phosphatase activity in cultures of rat bone marrow stromal cells. Further modification of 1 has led to the discovery of more potent 3-benzothiepin-2- carboxamide derivatives 2. Of these, 3-benzothiepin derivatives bearing a 4- (dialkoxyphosphorylmethyl)phenyl group on the 2-carboxamide moiety such as 2h and 2q exhibited significant improvement of activity compared to ipriflavone. Asymmetric synthesis of 2h and 2q revealed that the (-)-isomers possessed activities superior to those of the (+)-isomers. Further evaluation of these compounds using the mouse osteoblastic cell line MC3T3-E1 revealed that (-)- 2q enhanced the effect of bone morphogenetic protein. In addition, application of a sustained-release agent containing 2q increased the area of newly formed bone in a rat skull defect model. Based on these findings, (-)- 2q was selected for further investigation as a new drug stimulating bone formation. Synthesis and structure-activity relationships for this novel series of 2-benzothiopyran and 3-benzothiepin derivatives are detailed.

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

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The aim of protein tyrosine phosphatase 1B (PTP 1B) inhibitors is to develop effective drug for diabetes and obesity. Coumarin becomes as a good skeleton, and is often applied in drug design and synthesis. In this paper, we have synthesized a series of novel coumarin derivatives to be as potential PTP 1B inhibitors. The inhibition rate of compound 9 was more than 80%, and the IC50 value was 49.2 muM, which would be considered for further study.

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

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High ortho selectivity for Ir-catalyzed C-H borylations (CHBs) of anilines results when B2eg2 (eg = ethylene glycolate) is used as the borylating reagent in lieu of B2pin2, which is known to give isomeric mixtures with anilines lacking a blocking group at the 4-position. With this modification, high selectivities and good yields are now possible for various anilines, including those with groups at the 2- and 3-positions. Experiments indicate that ArylN(H)Beg species are generated prior to CHB and support the improved ortho selectivity relative to B2pin2 reactions arising from smaller Beg ligands on the Ir catalyst. The lowest-energy transition states (TSs) from density functional theory computational analyses have N-H···O hydrogen-bonding interactions between PhN(H)Beg and O atoms in Beg ligands. Ir-catalyzed CHB of PhN(H)Me with B2eg2 is also highly ortho-selective. 1H NMR experiments show that N-borylation fully generates PhN(Me)Beg prior to CHB. The TS with the lowest Gibbs energy was the ortho TS, in which the Beg unit is oriented anti to the bipyridine ligand.

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

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The present invention relates to novel compounds of formula (I) that are capable of inhibiting one or more kinases, especially SYK (Spleen Tyrosine Kinase), LRRK2 (Leucine-rich repeat kinase 2) and/or MYLK (Myosin light chain kinase) or mutants thereof. The compounds find applications in the treatment of a variety of diseases. These diseases include autoimmune diseases, inflammatory diseases, bone diseases, metabolic diseases, neurological and neurodegenerative diseases, cancer, cardiovascular diseases, allergies, asthma, alzheimer¿s disease, parkinson¿s disease, skin disorders, eye diseases, infectious diseases and hormone-related diseases.

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