cas 10354-00-4, DIBENZOSUBERENOL | Articles data

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Structures and vibrational spectra of 5H-dibenz[b,f]azepine and 5H-dibenzo[a,d]cycloheptene-5-ol on the basis of quantum mechanical calculations
Optimized geometries of NH-equatorial and NH-axial conformers of 5H-dibenz[b,f]azepine and CH-equatorial and CH-axial conformers of 5H-dibenzo[a,d]cyclohepten-5-ol have been obtained at the B3LYP and BLYP levels of the hybrid density functional theory with the 6-31G* and 6-31+G* basis sets. Corresponding ab initio calculations have also been performed at the HF/6-31G* level. For the investigated levels harmonic vibrational frequencies were calculated analytically. FT Raman (3200-200 cm-1) and infrared (3900-400 cm-1) spectra of 5H-dibenz[b,f]azepine and 5H-dibenzo[a,d]cyclohepten-5-ol have been recorded in the solid state and interpreted on a base of theoretical predictions.
Kuramshina,Mogi,Takahashi
p. 121 - 139
(2003)
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Thermal Extrusion of a One-Carbon Species from 1,2-Benzotropilidene (5H-benzocycloheptene), the Benzotropyl (Benzocycloheptenyl) Free Radical, 1,2:5,6-Dibenzotropilidene (5H-Dibenzocycloheptene), and the 1,2:4,5-Dibenzotropyl (Dibenzocycloheptenyl) Free Radical
The benzotropyl dimer 7,7'-bis(3,4-benzotropyl) (6) has been prepared and thermolyzed (400 deg C) both without and with added benzene.In addition, 1,2:5,6-dibenzotropilidene (3) and 7,7'-bis(1,2:5,6-dibenzotropyl) (7) have been pyrolyzed (430 deg C) both without and with added naphthalene.The similarity of the products obtained in the former pyrolysis, namely, naphthalene (12), α-methylnaphthalene (13), β-methylnaphthalene (14), 1,2-benzocyclohepta-1,3-diene (15), benzocycloheptene (16) and toluene (whwn benzene is used), with those obtained from pyrolysis of 1,2-benzotropilidene (1) confirms that both thermolyses involve the benzotropyl radical.The similarity of the products from the latter two pyrolyses (of 3 and 7), namely, anthracene (4), 9-methylanthracene (5), 9,10-dihydroanthracene (17), 1,2:4,5-dibenzo-1,4-cycloheptadiene (20), 1- and 2-methylanthracene (18 and 19), and, when naphthalene (12) was used, benzotropilidene (1) and 1- and 2-methylnaphthalene (13 and 14), shows that both of these go through a common intermediate, the 1,2:4,5-dibenzotropyl radical (8). 9-Methylanthracene (5) was shown to thermally produce anthracene (4) and 1- and 2-methylanthracene (18 and 19), but, even with this complication, anthracene (4) was shown to be a primary product from the pyrolysis of dibenzotropilidene (3).Attempts to use di-tert-butyl nitroxide (21) as an initiator (400 deg C) gave primarily Diels-Alder addition of the isobutylene formed by decomposition of the nitroxide with both 1,2:4,5-dibenzotropilidene (the product of a 1,5-hydrogen shift in 3) and 9-methylanthracene (5).A lower temperature (345 deg C) reaction of 3 with naphthalene in the presence of nitroxide 21 did produce anthracene (4) and benzotropilidene (1) in addition to the Diels-Alder adduct, confirming the free-radical nature of the reaction.Low-temperature control experiments employing the benzotropyl dimer (6) (280 deg C) and the dibenzotropyl dimer (7) (345 deg C) showed that they were undergoing cleavage to their respective radicals (2 and 8) and that these were giving product directly, rather than the benzo- and dibenzotropilidenes (1 and 3), which were being formed in the reactions by hydrogen abstraction, giving the products.It has thus been demonstrated that the benzo- and dibenzotropyl radicals (2 and 8) can transfer a CH group to an aromatic acceptor and that the pyrolytic reactions of benzo- and dibenzotropilidenes (1 and 3) to give naphthalene and anthracene are CH-transfer reactions of the tropyl radicals formed by hydrogen abstraction.Yields of up to 65percent of anthracene (4) have been realized in the pyrolyses of dibenzotropilidene (3).Mechanisms for these CH-transfer reactions are presented.A contrast is made between the low-temperature reaction of the dibenzotropyl dimer (7) which (345 deg C) gives only anthracene and dibenzotropilidene (3), by CH loss and hydrogen abstraction, respectively, and the low-temperature (280 deg C) reaction of benzotropyl dimer (6) which not only gives naphthalene (12) and benzotropilidene (1) by CH loss and hydrogen ...
Pomerantz, Martin,Combs, Gerald L.,Fink, Rina
p. 143 - 149
(1980)
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Labilization of C-N linkages by dibenzocyclohepten 5 yl ring system
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Maulding,Michaelis,Nazareno
p. 1908 - 1914
(1974)
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An efficient, large-scale synthesis of cytenamide
Dibenzosuberenone (5H-dibenzo[a,d]cyclohepten-5-one) was reduced to the corresponding alcohol by sodium borohydride/MeOH and converted to the corresponding 5-chloro compound by thionyl chloride/benzene, treatment of which with CuCN/toluene gave the corresponding nitrile. Hydrolysis by ethanolic KOH yielded the corresponding amide, cytenamide (5H-dibenzo[a,d]cycloheptene-5-carboxamide).
Bedford, Colin T.
p. 153 - 155
(2018)
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Childs,R.F. et al.
p. 2175 - 2183
(1972)
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Polycyclic pyridone derivative, pharmaceutical composition and application thereof
The invention belongs to the field of medicines, and relates to a polycyclic pyridone derivative, a pharmaceutical composition and application thereof. The polycyclic pyridone derivative is a compound as shown in a formula (I) or a stereoisomer, a tautomer, a nitric oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or prodrugs of the compound as shown in the formula (I). Compared with the existing similar compounds, the compound disclosed by the invention not only can well inhibit the replication of influenza viruses, but also has lower cytotoxicity.
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Paragraph 0131-0132

(2021/05/01)

Synthesis and Anti-Influenza Virus Effects of Novel Substituted Polycyclic Pyridone Derivatives Modified from Baloxavir
In this work, a series of novel substituted polycyclic pyridone derivatives were designed and synthesized as potent anti-influenza agents. The cytopathic effect (CPE) assay and cytotoxicity assay indicated that all of the compounds possessed potent anti-influenza virus activity and relatively low cytotoxicity; some of them inhibited the replication of influenza A virus (IAV) at picomolar concentrations. Further studies revealed that, at a concentration of 3 nM, three compounds (10a, 10d, and 10g) could significantly reduce the M2 RNA amounts and M2 protein expression of IAV and inhibit the activity of RNA-dependent RNA polymerase (RdRp). Among them, (R)-12-(5H-dibenzo[a,d][7]annulen-5-yl)-7-hydroxy-3,4,12,12a-tetrahydro-1H-[1,4]oxazino[3,4-c]pyrido[2,1-f][1,2,4]triazine-6,8-dione (10a) was found to be a promising anti-influenza drug candidate with good human liver microsomal stability, as well as with better selectivity index and oral bioavailability than Baloxavir.
Chen, Dawei,Gao, Zhenxiong,Hou, Jinqiang,Jiang, Yuyang,Tang, Lin,Wu, Weibin,Yan, Haiyan,Zhang, Cunlong
supporting information
p. 14465 - 14476
(2021/10/12)

Efficient Transfer Hydrogenation of Ketones using Methanol as Liquid Organic Hydrogen Carrier
Herein, we demonstrate an efficient protocol for transfer hydrogenation of ketones using methanol as practical and useful liquid organic hydrogen carrier (LOHC) under Ir(III) catalysis. Various ketones, including electron-rich/electron-poor aromatic ketones, heteroaromatic and aliphatic ketones, have been efficiently reduced into their corresponding alcohols. Chemoselective reduction of ketones was established in the presence of various other reducible functional groups under mild conditions.
Garg, Nidhi,Paira, Soumen,Sundararaju, Basker
p. 3472 - 3476
(2020/05/29)

Zinc(ii)-catalyzed Grignard additions to ketones with RMgBr and RMgI
Highly efficient alkylations and arylations of ketones with Grignard reagents (RMgBr and RMgI) have been developed using catalytic ZnCl2, Me3SiCH2MgCl, and LiCl. Tertiary alcohols were obtained in high yields with high chemoselectivities, while minimizing undesired side products produced by reduction and enolization.
Hatano, Manabu,Ito, Orie,Suzuki, Shinji,Ishihara, Kazuaki
supporting information; experimental part
p. 2674 - 2676
(2010/07/08)

Zinc(II)-catalyzed addition of grignard reagents to ketones
(Figure presented) The addition of organometallic reagents to carbonyl compounds has become a versatile method for synthesizing tertiary and secondary alcohols via carbon-carbon bond formation. However, due to the lack of good nucleophilicity or the presence of strong basicity of organometallic reagents, the efficient synthesis of tertiary alcohols from ketones has been particularly difficult and, thus, limited. We recently developed highly efficient catalytic alkylation and arylation reactions to ketones with Grignard reagents (RMgX: R = alkyl, aryl; X = Cl, Br, I) using ZnCl2, Me3SiCH 2MgCl, and LiCl, which effectively minimize problematic side reactions. In principle, RMgBr and RMgI are less reactive than RMgCl for the addition to carbonyl compounds. Therefore, this novel method with homogeneous catalytic ZnCl2·Me3SiCH2MgCl·LiCl is quite attractive, since RMgBr and RMgI, which are easily prepared and/or commercially available, like RMgCl, can be applied successfully. As well as ketones and aldehydes, aldimines were effectively applied to this catalysis, and the corresponding secondary amines were obtained in high yield. With regard to mechanistic details concerning β-silyl effect and salt effect, in situ-prepared [R(Me3SiCH2)2Zn] -[Li]+[MgX2]m[LiCl]n (X = Cl/Br/I) is speculated to be a key catalytic reagent to promote the reaction effectively. The simplicity of this reliable ZnCl2·Me 3SiCH2MgCl·LiCl system in the addition of Grignard reagents to carbonyl compounds might be attractive for industrial as well as academic applications.
Hatano, Manabu,Ito, Orie,Suzuki, Shinji,Ishihara, Kazuaki
supporting information; experimental part
p. 5008 - 5016
(2010/10/04)

Flow-vacuum pyrolysis of dibenzocycloheptane derivatives on zeolites catalysts. IV
The pyrolysis of 10,11-dihydro-5H-dibenzo[a,d]cicloheptadien-5-ol (4) and of 5H-dibenzo[a,d]cycloheptatrien-5-ol (5) in flowvacuum conditions (advanced vacuum, inert atmosphere) on zeolites at 300°C is presented. The reaction products were identified by GC/MS using authentic samples and a reaction mechanisms involving cationic species as intermediates were proposed. A comparison with the pyrolysis of the same compounds performed in FVP conditions on quartz is presented.
Istrati, Daniela,Parvulescu, Luminitza,Popescu, Angela,Mihaiescu, Dan,Badea, Florin
p. 711 - 714
(2011/10/02)

NOVEL DIARYLALKENE DERIVATIVES AND NOVEL DIARYLALKANE DERIVATIVES
The invention relates to a compound represented by the following general formula (1) or its analogue, which selectively inhibit N-type calcium channels or its analogue, and to a method for treating pain etc. comprising the compound represented by the following general formula (1) or its analogue to a patient in need of such treatment: wherein, A represents CH=CH, etc., a, b, c and d represents CH etc., R1, R2, R3, R4, R5 and R6 represents H etc., V--W represents C=C, etc., n represents 0 to 3, Y1 represents O etc., B represents--(CH2)vCHR21 wherein v is 0 to 3, R21 represents H, a lower alkyl group or the like, etc., G represents--CO--, a covalent bond, etc., m is 0 to 6, R7 and R8 represents H, a lower alkyl group,--COR18a,--COOR20 wherein R18a and R20 each represents a lower alkyl group or the like, etc.
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Page 29-30

(2008/06/13)

MEDICINAL COMPOSITIONS CONTAINING GABAPENTIN OR PREGABALIN AND N-TYPE CALCIUM CHANNEL ANTAGONIST
The present invention relates to a pharmaceutical composition useful for preventing/treating pain, which comprises combination of gabapentin or pregabalin, or pharmaceutically acceptable salts thereof and N-type calcium channel antagonists or pharmaceutically acceptable salts thereof such as a compound having the following structure.
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Page/Page column 42-43

(2010/02/09)

Luminescent element material, luminescent element, ethylene derivative having n-containing 7-membered ring, and benzoazepine derivative
Disclosed are a luminescent element material comprising a polymer having a partial structure represented by formula (I) and a luminescent element usin the same.
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(2008/06/13)

Polycyclic phosphiranes: Synthesis of C-substituted BABAR-Phos compounds
BABAR-Phos is a very stable polycyclic phosphirane which is easily synthesized in few steps from dibenzosuberenone. BABAR-Phos is remarkably stable and is not oxygenated with O2 nor does it react with sulfur in boiling toluene. BABAR-Phos can be used as a ligand in homogenous catalysis. Substituents at the carbon of the PC2 heterocycle can be introduced and asymmetric BABAR-Phos were prepared. The coordination chemistry of rhodium complexes containing these as ligands was investigated.
Laeng, Florian B.,Gruetzmacher, Hansjoerg
p. 187 - 190
(2007/10/03)

Flow-vacuum pyrolysis of polycyclic compounds. 151 pyrolysis of three RELATED dibenzocycloalkanols
The flow-vacuum pyrolyses of cis-9,10-bis(hydroxymethyl)-9,10-dihydroanthracene (4); 6H-5,7-dihydrodibenzo[a,c]cyclohepten-6-ol (5) and 5H-dibenzo[a,d]cyclohepten-5-ol (6) were studied at 1.33 mbar in argon atmosphere over a large temperature interval. The main pyrolysis product of 4-cis was anthracene (13), accompanied by traces of 9-methylanthracene (15) and 9-anthraldehyde (14). The main pyrolysis products of 5 were: 9-methylphenanthrene (17) and 5H-dibenzo[a,c]cycloheptene (16), whereas phenanthrene (19) and fluorene (18) were minor products. From the flow-vacuum pyrolysis of 6 the corresponding ketone (dibenzosuberenone 12) and 5H-dibenzo[a,d]cycloheptene (20) were the major products and anthracene and 9-methylanthracene the minor ones. The thermal behavior of 4-cis, 5 and 6 was rationalized on the basis of mechanisms including radical and concerted steps. Some parts of the here proposed mechanisms were confirmed by our previous works describing the conversions of authentic 16 and 20 to the same end-products: 17 + 19, respectively 13 + 15. A comparison with the thermal behaviour of other related dibenzocycloalkanols is also made.
Banciu, Mircea D.,Popescu, Angela,Parvulescu, Lumini?a,Ciuculescu, Crinu,Drǎghici, Constantin,Banciu, Anca,Mihǎiescu, Dan
p. 239 - 248
(2007/10/03)

Benzylphosphonic acid inhibitors of human prostatic acid phosphatase
A series of α-substituted benzylphosphonic acids is described as inhibitors of human prostatic acid phosphatase, an enzyme has been used as a model to study aryl phosphatases. The most potent inhibitors in this series are 2-trifluoromethylbenzhydrylphosphonic acid (9 μM), and α-(2-phenylethyl)benzylphosphonic acid (14 μM). The structure-activity studies suggest that bulk tolerance beyond the phosphate binding area limits the steric or hydrophobic contribution to inhibitor potency achieved through α-carbon substitution.
Schwender,Beers,Malloy,Cinicola,Wustrow,Demarest,Jordan
p. 311 - 314
(2007/10/03)

Ritter Reactions. IX. Transannular Addition of Nitriles to the 5H-Dibenzocycloheptene Ring System
The 5H-dibenzocyclohepten-5-ols (1a-e) undergo sequential intramolecular and conventional Ritter reactions with acetonitrile to afford the cyclohepten-11-yl>acetamides (6a-e).Typical yields for these one-flask conversions are 52-64percent, except for the reaction of (1a) where production of the dimeric substance (4a) is favoured.Alcohol (1a) can provide either type of product in good yield, depending on the conditions employed, when reacted with benzonitrile.The molecular skeleton present in the adducts (6) has been confirmed by determination of the crystal structure of (6c) , a 9.188(3), b 14.632(5), c 16.563(9) Angstroem, α 115.64(9), β 90.92(2), γ 96.29(2) deg, Z 4, R 0.043>.
Pich, Kim C.,Bishop, Roger,Craig, Donald C.,Scudder, Marcia L.
p. 837 - 852
(2007/10/02)

Structure-Activity Studies on Benzhydrol-Containing Nipecotic Acid and Guvacine Derivatives as Potent, Orally-Active Inhibitors of GABA Uptake
The introduction of lipophilic groups onto the ring nitrogen of nipecotic acid and guvacine, two known GABA uptake inhibitors, afforded potent, orally-active anticonvulsant drugs.A series of compounds is reported which explores the structure-activity relationships (SAR) in this series.Among the areas explored: side-chain SAR (aromatic-, heterocyclic-, and tricyclic-containing side chains) and modifications to the tetrahydropyridine ring.The benzhydrol ether-containing side chains afforded the most potent compounds with several exhibiting in vitro IC50 values for GABA uptake of 1 μM (including 5, Table I; 37, 43, Table IV; and 44, Table V).Compound 44 was selected for extensive evaluation and subsequently progressed to Phase 1 clinical trials with severe adverse effects seen after single dose administration to humans.
Pavia, Michael R.,Lobbestael, Sandra J.,Nugiel, David,Mayhugh, Daniel R.,Gregor, Vlad E.,et al.
p. 4238 - 4248
(2007/10/02)

N-substituted 3-piperidine-or 3-pyridine-carboxylic acids and derivatives thereof
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(2008/06/13)

Various N-substituted 3-piperidine carboxylic acids or N-substituted 3-pyridinecarboxylic acids and derivatives thereof
Selected analogs of nipecotic acid are the novel compounds of the present invention. The analogs are GABA uptake inhibitors for use to treat epilepsy and, thus, the invention is also pharmaceutical compositions and methods of use therefor.
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(2008/06/13)

Contrasting Photosolvolytic Reactivities of 9-Fluorenol vs 5-Suberenol Derivatives. Enhanced Rate of Formation of Cyclically Conjugated Four ? Carbocations in the Excited State
The photosolvolysis of 9-fluorenol (1) and several of its derivatives, as well as related systems, has been studied in aqueous methanol and acetonitrile solutions.The primary aim of this study was to examine the effect of the internal cyclic array (ICA) of these compounds in promoting photosolvolysis with respect to the number of ? electrons available in the ICA.It was observed that 9-fluorenol derivatives photosolvolyze much more efficiently than any of the related systems studied in this work.In contrast, ground-state 9-fluorenol derivatives are the least reactive systems with respect to solvolysis.Quantum yields for methyl ether formation for photosolvolysis in 50percent MeOH-H2O are reported for 1-3.Rate constants for solvent-assisted photodehydroxylation (ks) are calculated on the basis of the proposed mechanism of heterolytic C-OH bond rupture in the primary photochemical step and are in the range (1.3-1.6)x1E10 s-1 for 1-3.
Wan, Peter,Krogh, Erik
p. 4887 - 4895
(2007/10/02)

Various N-substituted 3-piperidine carboxylic acids or N-substituted 3-pyridinecarboxylic acids and derivatives thereof
Analogs of nipecotic acid are the novel compounds of the present invention. The analogs are GABA uptake inhibitors for use to treat epilepsy and, thus, the invention is also pharmaceutical compositions and methods of use therefor.
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(2008/06/13)

4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine compounds, pharmaceutical compositions and methods
Pharmaceutical compositions comprising 4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine compounds and the use of 4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine compounds for treatment of certain cardiovascular disorders are disclosed.
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(2008/06/13)

DIAZO COMPOUNDS-66 5-(DIAZOMETHYL)-5H-DIBENZOCYCLOHEPTENES - INTERMEDIATES ON THE WAY TO NEW DIBENZOSEMIBULLVALENE AND DIBENZOCYCLOOCTENE SYNTHESES
Electrophilic diazoalkane substitution of (silver diazomethyl)phosphoryl or mercury bis compounds (10a-c or 12a-c) with 5-chloro-5H-dibenzocycloheptene (6) furnishes the 5-(diazomethyl)-5H-dibenzocycloheptenes (8a-c or 13a-c).Copper(II) acetylacetonate-catalysed decomposition of these compounds in toluene results, in all cases, the formation of dibenzosemibullvalenes (17a-f).In addition, the dibenzocyclooctenes 16a-e and, in the cxase of 13c, the dibenzoheptefulvene 18f are formed.
Boehshar, Manfred,Heydt, Heinrich,Regitz, Manfred
p. 1815 - 1822
(2007/10/02)

Tricyclic pharmacological agents, intermediates and methods of making
5-(3-Substituted prop-cis-1-enyl)- and 5-(3-substituted prop-trans-1-enyl)- derivatives of 5H-dibenzo[a,d]cycloheptenes and 10,11-dihydro-5H-dibenzo[a,d]cycloheptenes and methods of making. The process of preparing the 5-(3-substituted prop-cis-1-enyl)- derivatives comprises hydrogenation of the appropriate 5-(3-substituted prop-1-ynyl)- derivatives in the presence of a noble metal catalyst. The 5-(3-substituted prop-trans-1-enyl)- derivatives can be prepared via treatment of the appropriate 5-(3-substituted prop-1-ynyl)- derivative with an alkali metal (e.g. sodium) in the presence of ammonia. Both the 5-(3-amino-cis- and 3-amino-substituted prop-trans-1-enyl)- derivatives exhibit antihistamine activity and are further useful in the treatment of, and/or palliation of, abnormal conditions occurring in mammals, related to the central nervous system. The remaining compounds have utility as intermediates for pharmacologically active compounds.
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(2008/06/13)