Search results for "cyclic"

Synthesis and Biological Properties of Benzothiazole, Benzoxazole, and Chromen-4-one Analogues of the Potent Antitumor Agent 2-(3,4-Dimethoxyphenyl)-…

2008

New fluorinated 2-aryl-benzothiazoles, -benzoxazoles, and -chromen-4-ones have been synthesized and their activity against MCF-7 and MDA 468 breast cancer cell lines compared with the potent antitumor benzothiazole 5. Analogues such as 9a, b and 12a, d yielded submicromolar GI50 values in both cell lines; however, none of the new compounds approached 5 in terms of antitumor potency. For 5, binding to the aryl hydrocarbon receptor appeared to be necessary but not sufficient for growth inhibition.

Chemistry inside molecular containers in the gas phase.

2013

Inner-phase chemical reactions of guest molecules encapsulated in a macromolecular cavity give fundamental insight into the relative stabilization of transition states by the surrounding walls of the host, thereby modelling the situation of substrates in enzymatic binding pockets. Although in solution several examples of inner-phase reactions are known, the use of cucurbiturils as macrocyclic hosts and bicyclic azoalkanes as guests has now enabled a systematic mass spectrometric investigation of inner-phase reactions in the gas phase, where typically the supply of thermal energy results in dissociation of the supramolecular host-guest assembly. The results reveal a sensitive interplay in wh…

Kinetics of the Strain-Promoted Oxidation-Controlled Cycloalkyne-1,2-quinone Cycloaddition: Experimental and Theoretical Studies

2018

Stimulated by its success in both bioconjugation and surface modification, we studied the strain-promoted oxidation-controlled cycloalkyne–1,2-quinone cycloaddition (SPOCQ) in three ways. First, the second-order rate constants and activation parameters (ΔH⧧) were determined of various cyclooctynes reacting with 4-tert-butyl-1,2-quinone in a SPOCQ reaction, yielding values for ΔH⧧ of 4.5, 7.3, and 12.1 kcal/mol, for bicyclo[6.1.0]non-4-yne (BCN), cyclooctyne (OCT), and dibenzoazacyclooctyne (DIBAC), respectively. Second, their reaction paths were investigated in detail by a range of quantum mechanical calculations. Single-configuration theoretical methods, like various DFT and a range of MP2…

Asymmetric Organocatalytic Michael Addition–Cyclization Cascade of Cyclopentane-1,2-dione with Substituted α,β-Unsaturated Aldehydes

2017

An asymmetric organocatalytic Michael addition–cyclization cascade reaction has been developed using cyclopentane-1,2-dione as a Michael donor and α,β-unsaturated aldehydes as Michael acceptors. Bicyclic hemiacetals were obtained in excellent yields and enantioselectivities. On the basis of the results, a one-pot reaction has been developed to obtain chiral 3-substituted cyclopentane-1,2-diones and substituted dihydropyrans in good yields and excellent enantioselectivity.

Dependence of the Substituent Effect on Solvent Properties

2018

The influence of a solvent on the substituent effect (SE) in 1,4-disubstituted derivatives of benzene (BEN), cyclohexa-1,3-diene (CHD), and bicyclo[2.2.2]octane (BCO) is studied by the use of polarizable continuum model method. In all X–R–Y systems for the functional group Y (NO2, COOH, OH, and NH2), the following substituents X have been chosen: NO2, CHO, H, OH, and NH2. The substituent effect is characterized by the charge of the substituent active region (cSAR(X)), substituent effect stabilization energy (SESE), and substituent constants σ or F descriptors, the functional groups by cSAR(Y), whereas π-electron delocalization of transmitting moieties (BEN and CHD) is characterized by a geo…

1H and13C NMR assignments and conformational analysis of some tetracyclic compounds with a bicyclo[4.2.0]octane ring system

1998

Rhodium(III)-catalyzed ring-opening of strained olefins through C–H activation of O-acetyl ketoximes: an efficient synthesis of trans-functionalized …

2013

An efficient strategy for the stereoselective synthesis of functionalized cyclopentenes and spiro[2.4]heptenes from strained olefins via C–H activation of aryl ketone O-acetyl ketoximes using [RhCl2Cp∗]2 catalyst is described. The results revealed that a wide range of readily accessible aryl and heteroaryl ketoximes are compatible in this method for the ring opening of bicyclic and spirotricyclic olefins.

Dimeres und Trimers 1-Methyl-1-aza-5-stannabicyclo[3.3.01,5]-octan sulfid [MeN(CH2CH2CH2)2SnS]n, Röntgenstrukturanalyse des Dimeren und Gleichgewicht…

1991

Abstract The crystal structure of the dimeric title compound has been determined and refined to R = 0.0266. The core of the nearly centrosymmetric dimer is formed by an almost perfect [SnS]2 rectangle (Sn-S 2.39 and 2.51 A). The two sulfur atoms of this rectangle establish the connecting edge of two distorted trigonal bipyramids around the two tin atoms (Sn … N 2.55 A). Solutions of the title compound contain in addition to the dimer (σ(119Sn) = −4.6 ppm) about 20% of the trimer (+ 10.3 ppm). By quick crystallization a mixture of both oligomers can be transferred into the solid state.

Elektronenstoß-induzierte massenspektrometrische Fragmentierung von 2,2′-Bisindolylmethoxy- und Trisindolyl-methanen

1986

An exclusive approach to 3,4-disubstituted cyclopentenes and alkylidene cyclopentenes via the palladium catalyzed ring opening of azabicyclic olefins…

2013

A simple and efficient method for the stereoselective ring opening of bicyclic hydrazines with various aryl halides under palladium catalysis has been elaborated. The reactions afforded trans-3,4-disubstituted cyclopentenes or alkylidene cyclopentenes in good to excellent yields. By taking advantage of multiple points of functionalization in the synthesized trans-3-phenyl-4-hydrazino-cyclopentene, we have synthesized the antidepressant Cypenamine (trans-2-phenylcyclopentylamine).