4747-72-2Relevant articles and documents
Microwave, Infrared, and Raman Spectra, Conformational Stability, Structure, Dipole Moment, and Vibrational Assignment for Cyclopropyl Isocyanate
During, J. R.,Berry, R. J.,Wurrey, C. J.
, p. 718 - 726 (1988)
The microwave spectrum of cyclopropyl isocyanate, c-C3H5NCO, has been recorded from 18.5 to 40.0 GHz.Two sets of a-type, R-branch transitions have been observed and assigned, on the basis of the rigid rotor model, to the trans and the cis conformers, which have the isocyanate moiety oriented in an s-trans or s-cis fashion, respectively, relative to the three-membered ring.In addition to the ground vibrational state transitions, lines due to two excited states of the CNC bend and four excited states of the asymmetric torsion for the trans conformer, as well as one torsional excited state for the cis form, have been assigned.The B and C rotational constants for the ground vibrational state of the trans and cis conformers are the following: B=1784.303 +/- 0.003, C=1716.133 +/-0.003 and B=2186.797 +/-0.010, C=2106.242 +/- 0.010 MHz, respectively.The values of the A rotational constants for both conformers were not well determined because the measured transitions are not very sensitive to these constants.From the relative intensity measurements in the microwave spectrum, the torsional frequency is estimated to be 24 cm-1 for the trans conformer and 14 cm-1 for the cis form.The dipol moment components determined from the Stark effect are /μa/=2.56 +/- 0.02, /μc/=0.71 +/- 0.03, and /μt/=2.65 +/- 0.02 D for the trans conformer and /μa/=2.720 +/-0.004, /μb/=0.17 +/-0.01, and /μt/=2.726 +/- 0.001 D for the cis conformer.With reasonably assumed sructural parameters for the cyclopropyl moiety and bond distances for the isocyanate group, estimates of the differences between the cis and trans conformers of the title molecule for the following parameters were made: r(C-N), -1) and Raman (3300 to 10 cm-1) spectra have been recorded for the gas and the solid states.Additionally, the Raman spectrum of the liquid has been recorded and qualitative depolarization values have been obtained.Based on the band contours, depolarization values, and group frequencies, the normal vibrational modes have been assigned.From a temperature study of the Raman lines of an assigned conformer pair in the liquid phase, the value of ΔH between conformers has been determined to be 39 +/- 5 cm-1, with the trans form being more stable.However, from the Raman spectrum of the solid the cis conformer has been determined to be the preferred form in the crystal.These results are compared with the corresponding quantities in some similar molecules.
Design, synthesis and antitumor assessment of phenylureas bearing 5-fluoroindolin-2-one moiety
Cai, Yunrui,Chen, Tong,Zhu, Huajian,Zou, Hongbin
, p. 958 - 968 (2020/08/19)
Background: The development of novel antineoplastic agents remains highly desirable. Objective: This study focuses on the design, synthesis, and antitumor evaluation of phenyl ureas bearing 5-fluoroindolin-2-one moiety. Methods: Three sets of phenylureas were designed and synthesized and their antiproliferative abil-ity was measured against four human carcinoma cell lines (Hela, Eca-109, A549, and MCF-7) via MTT assay. In vivo anticancer activity was further evaluated in xenograft models of human breast cancer (MCF-7). Results: A total of twenty-one new compounds were synthesized and characterized by means of1 H and13 C NMR as well as HR-MS. Three sets of compounds (1a?1c, 2a?2c, and 3a?3c) were ini-tially constructed, and preliminary antiproliferative activities of these molecules were evaluated against Hela, Eca-109, A549 and MCF-7, highlighting the meta-substituted phenylureas (1a?1c) as the most cytotoxic set. A series of meta-substituted phenylureas derivatives (1d?1o) were then designed and synthesized for structure-activity relationship study. Most of the new compounds showed desirable cytotoxicity, among which compound 1g exhibited the most remarkable cyto-toxic effects against the tested human cancer cells with IC50 values ranging from 1.47 to 6.79 μM. Further studies showed that compound 1g suppressed tumor growth in human breast cancer (MCF-7) xenograft models without affecting the body weight of its recipients. Conclusion: In this study, twenty-one new compounds, containing the privileged structures of phenylurea and 5-fluoroindolin-2-one, were designed and synthesized. Subsequent structure-activity studies showed that 1g was the most bioactive antitumor agent among all tested com-pounds, hence a potentially promising lead compound once given further optimization.
NITROGEN-CONTAINING HETEROCYCLIC COMPOUND AND USE OF SAME
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Page/Page column 171, (2011/07/06)
The present invention relates to a compound represented by the formula wherein ring A is a nitrogen-containing heterocycle; ring B is an aromatic ring optionally having substituent(s); ring D is an aromatic ring optionally having substituent(s); L is a group represented by the formula R2, R3, R4a and R4b are each independently a hydrogen atom, an optionally halogenated C1-6 alkyl group or an optionally halogenated C3-6 cycloalkyl group, or R2 and R3 are optionally bonded via an alkylene chain or an alkenylene chain, or R4a and R4b are optionally bonded via an alkylene chain or an alkenylene chain; R1 is a hydrogen atom or a substituent; m and n are each independently an integer of 0 to 5; m+n is an integer of 2 to 5; and- - - is a single bond or double bond, or a salt thereof; and the like. The compound has a superior tachykinin receptor antagonistic action, and is useful as an agent for the prophylaxis or treatment of various diseases such as lower urinary tract diseases, digestive tract diseases, central neurological disease and the like.
Azide monoliths as convenient flow reactors for efficient Curtius rearrangement reactions
Baumann, Marcus,Baxendale, Ian R.,Ley, Steven V.,Nikbin, Nikzad,Smith, Christopher D.
experimental part, p. 1587 - 1593 (2008/10/09)
The preparation and use of an azide-containing monolithic reactor is described for use in a flow chemistry device and in particular for conducting Curtius rearrangement reactions via acid chloride inputs. The Royal Society of Chemistry 2008.
DERIVATIVES AND ANALOGS OF CHROMAN AS FUNCTIONALLY SELECTIVE ALPHA2C ADRENORECEPTOR AGONISTS
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Page/Page column 77, (2008/12/08)
In its many embodiments, the present invention provides a novel class of chroman compounds of formula I as α2C adrenergic receptor agonists, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of prepaxing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more conditions associated with the α2C adrenergic receptors using such compounds or pharmaceutical compositions.
PYRAZINE DERIVATIVES USEFUL AS ADENOSINE RECEPTOR ANTAGONISTS
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Page/Page column 157-158, (2008/06/13)
The present invention provides a compound of formula (I) wherein: A represents an optionally substituted monocyclic or polycyclic aryl or heteroaryl group B represents an optionally substituted monocyclic nitrogen-containing heteroaryl group ; and either a) R1 and R2 represent hydrogen or specified substituents, or b) R2, R1 and the -NH- group to which R1 is attached, form a moiety selected from the moiety of formulae (IIa) and (IIb): (IIa) These compounds are useful as antagonists of the A2B receptor, for instance in the treatment of asthma.
COMPOUNDS, COMPOSITIONS CONTAINING THEM, PREPARATIONS THEREOF AND USES THEREOF II
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Page/Page column 82; 83; 100, (2010/10/20)
Compounds of Formulae I, or pharmaceutically acceptable salts thereof: (I) wherein R1, R2, R3, R4 and G are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.
Substituted analogues of GV150526 as potent glycine binding site antagonists in animal models of cerebral ischemia
Di Fabio, Romano,Conti, Nadia,De Magistris, Elisabetta,Feriani, Aldo,Provera, Stefano,Sabbatini, Fabio Maria,Reggiani, Angelo,Rovatti, Luca,Barnaby, Robert J.
, p. 3486 - 3493 (2007/10/03)
A series of analogues of the indole-2-carboxylate GV150526, currently in clinical trials as a potential neuroprotective agent for the control of the cerebral damage after stroke onset, was designed based on previous studies dealing with the electronic features of the north-east region of the glycine binding site associated with the NMDA receptor. In particular, the substitution of the para position of the terminal phenyl ring of GV150526 with suitable hydrophilic groups resulted in the identification of a new class of glycine antagonists. These compounds exhibited nanomolar in vitro affinity to the glycine binding site, high receptor selectivity, and outstanding in vivo potency. In particular, 3-[(E)-2-[(4- ureidomethylphenyl)aminocarbonyl]ethenyl]-4,6-dichloroindole-2-carboxylic acid was found to be highly effective in the middle cerebral artery occlusion (MCAo) model in the rat, an animal model of focal ischemia, when given both prior to and after the occlusion of the middle cerebral artery. Notably, a significant neuroprotective effect was seen in this model postischamia, when the administration of this compound was delayed up to 6 h from the occlusion of the middle cerebral artery, further confirming the wide therapeutic window seen for GV150526A.
N-Cyclopyopyl-N-(fluorophenyl)-N-acylureas and their herbidical use
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, (2008/06/13)
Certain N'-cyclopropyl-N-(fluorophenyl)-N-acylureas, useful as selective herbicides.
