- Bifunctional antitumor agents. Derivatives of pyrrolo[9,10-b]phenanthrene - A DNA intercalative delivery template
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The preparation and intercalative ability of the pyrrolo[9,10-b]phenanthrene nucleus is described. Functionalization of the nucleus was achieved using standard indole chemistry. The utility of this template as a DNA intercalating drug delivery system is demonstrated by synthesis of a derived bis-chloroethylamine alkylating system and a hybrid DNA interactive enediyne system.
- Jones, Graham B.,Mathews, Jude E.
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- Enantioselective Lewis Acid Catalyzed ortho Photocycloaddition of Olefins to Phenanthrene-9-carboxaldehydes
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Visible-light irradiation (λ=457 nm) enabled the enantioselective ortho photocycloaddition of olefins to phenanthrene-9-carboxaldehydes (15 examples, 46–93 % yield, 82–98 % ee). A chiral oxazaborolidine Lewis acid (20 mol %) was employed as the catalyst. It operates by coordination to the aldehyde inducing a bathochromic absorption shift beyond the nπ* absorption of the uncomplexed aldehyde. At long wavelengths the Lewis acid complex is exclusively excited; within the complex, one enantiotopic face of the aromatic aldehyde is efficiently shielded. Lewis acid coordination also alters the type selectivity and the simple diastereoselectivity of the photocycloaddition.
- Stegbauer, Simone,Jandl, Christian,Bach, Thorsten
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supporting information
p. 14593 - 14596
(2018/10/15)
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- Microwave-assisted Vilsmeier-Haack formylation of aromatic substrates
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A microwave-assisted Vilsmeier-Haack formylation reaction has been studied on various amines, phenols and polynuclear hydrocarbons under solvent free condition that rapidly affords higher yield of products compared to traditional thermal condition.
- Ghosh, Kumaresh,Adhikari, Suman
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experimental part
p. 959 - 961
(2009/12/24)
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- Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction
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Stereocontrolled synthesis of novel β-lactams using polyaromatic imines following the Staudinger reaction has been accomplished. The effects of domestic microwave irradiation on this type of reaction have been investigated. Formation of trans-β-lactams has been explained through isomerization of the enolates formed during the reaction of acid chloride (equivalent) with imines in the presence of triethylamine. A donor-acceptor complex pathway is believed to be involved in the formation of cis-β-lactams. The effect of a peri hydrogen has been found to be significant in controlling the stereochemistry of the resulting β-lactams. SAR has identified β-lactams with anticancer activity. The presence of an acetoxy group has proven obligatory for their anticancer activity.
- Banik, Bimal K.,Banik, Indrani,Becker, Frederick F.
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p. 3611 - 3622
(2007/10/03)
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- Therapeutics for chemokine mediated diseases
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The invention provides therapeutic and biological uses of chemokine-receptor-binding compounds (including chemokine receptor ligands such as chemokine receptor agonists or antagonists), such as tricyclic phenanthrene derivatives, including uses in the treatment of disease states mediated by chemokines. The relevant chemokines may for example be monocyte chemoattractant protein-one (MCP-1) or interleukin-8 (IL-8), and the relevant chemokine receptors may for example be corresponding chemokine receptors (CCR-2, CCR-4, CXCR-1, and CXCR-2). In other aspects, the invention provides corresponding pharamaceutical compositions and therapeutic methods. In one aspect, for example, the invention provides for the use of phenanthrene-9,10-dione in the treatment of multiple sclerosis.
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- Vilsmeier reagent for formylation in solvent-free conditions using microwaves
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POCl3-DMF over silica gel has been used for the synthesis of β-chlorovinylaldehydes (1-5), 2-aryl-3-formylindoles (6-8), 2-chloro-3-formylquinolines (9-13) and other aromatic aldehydes (14-20) using solvent-free conditions and microwave irradiation.
- Paul,Gupta,Gupta
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p. 1115 - 1118
(2007/10/03)
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- A new method of acylation and formylation of polycyclic aromatic hydrocarbons
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Polycyclic aromatic hydrocarbon radical anions, prepared by the addition of sodium to the aromatic hydrocarbon in THF, undergo acylation with carboxylic acid esters and formylation with N,N-dialkylformamides.
- Periasamy, Mariappan,Rama Reddy, Malladi,Bharathi, Pandi
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p. 677 - 683
(2007/10/03)
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- Barium Permanganate, Ba(MnO4)2, a versatile and mild oxidizing agent for use under aprotic and non-aqueous conditions
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Barium Permanganate is an easily prepared, stable, and a versatile oxidation reagent. With this reagent different types of primary and secondary hydroxy compounds are converted to their carbonyl derivatives. Aldehydes could be transformed to their carboxylic acids. Benzylic chloride and bromides are converted to their aldehydes and carboxylic acids. Semicarbazide and 2,4-dinitrophenylhydrazine derivatives of benzylic carbonyl compounds undergo carbon-nitrogen bond cleavage selectively and yield the expected carbonyl compounds. p-Hydroquinone is converted to p-benzoguinone and aromatic amines to their azo compounds. Anthracene and phenanthrene produce their 9,10-quinones. Diphenyl acetylene and trans stilbene give benzil, and styrene produces benzaldehyde. Selective oxidations of secondary benzylic carbon-hydrogen bonds occur and the corres- ponding carbonyl compounds are produced in good yields.
- Firouzabadi,Seddighi,Mottaghineiad,Bolourchian
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p. 6869 - 6878
(2007/10/02)
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- Selective Oxidative Cleavage of Benzylic Carbon-Nitrogen Double Bonds Under Non-Aqueous Condition with Tetrakis(pyridine)-silver Dichromate 2Cr2O7
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Carbonyl derivatives of phenylhydrazine, 2-nitrophenylhydrazine, 2,4-dinitrophenylhydrazine, semicarbozone, and hydroxylamine are converted to their corresponding carbonyl compounds with tetrakis(pyridine)silver dichromate in benzene.Selectivity is also observed for benzylic C=N cleavage.
- Firouzabadi, H.,Seddighi, M.,Ahmadi, Z. Arab,Sardarian, A. R.
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p. 3385 - 3396
(2007/10/02)
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- BARIUM PERMANGANATE A USEFUL OXIDANT FOR THE SELECTIVE DEOXIMATION OF BENZYLIC OXIMES TO THEIR CORRESPONDING CARBONYL COMPOUNDS
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Benzylic oximes are oxidized selectively with barium permanganate in refluxing acetonitrile and produce their corresponding carbonyl compounds in good yields.
- Firouzabadi, H.,Mottaghineiad, E.,Seddighi, M.
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p. 3469 - 3476
(2007/10/02)
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- Process for nucleophilic fluoroalkylation of aldehydes
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Aryl difluoromethyl sulfone adds to alkehydes under phase transfer conditions to give novel substituted alcohols of the general formula wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
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- Preparation and Chemical Behaviour of exo-Methylene Compounds: Isoelectronic Compounds of 5-Methylenecyclohexa-1,3-diene
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Some exo-methylene compounds such as 9-methylene-9,10-dihydrophenanthrene(2) were photolytically prepared and their chemical behaviour was investigated.Treatment of (2) with acid (CF3CO2H) or base (OBut(1-)) led to the formation of 9-methylphenanthrene, with bromine to 9-bromomethylphenanthrene.Reaction with dimethyl acetylenedicarboxylate did not give Diels-Alder adduct but give an ene adduct.Treatment with ethenetetracarbonitrile also gave an ene adduct.Reaction with carbene or carbenoids gave 9,10-dihydrophenanthrene-9-spirocyclopropanes.Reaction with ethenetetracarbonitrile was examined for other exo-methylene compounds, 1-methylene-1,2-dihydronaphtalene and 2-methylene-2,3-dihydrobenzothiophene.The aromatisation may be responsible for the reactions of these exo-methylene compounds except for the reaction with carbenes.
- Sugimoto, Akira,Yamano, Junzo,Yasueda, Masahiro,Yoneda, Shigeo
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p. 2579 - 2584
(2007/10/02)
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- BIS(2,2'-BIPYRIDYL)COPPER(II) PERMANGANATE (BBCP): A MILD AND VERSATILE OXIDANT IN ORGANIC SYNTHESIS
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The preparation of bis(2,2'-bipyridyl)copper(II) permanganate (BBCP) is described.The reagent converts alcohols to the corresponding carbonyl compounds, α-hydroxy ketones to diketones, hydroquinone to p-benzoquinone, and compounds with benzylic double bonds to benzaldehyde in high yield.Benzophenone oxime, acetophenone oxime and various benzaldoximes are converted to the corresponding carbonyl compounds, aromatic amines to azo compounds, and benzylamine to benzaldehyde, usually in high yields, under mild condition.
- Firouzabadi, H.,Sardarian, A. R.,Naderi, M.,Vessal, B.
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p. 5001 - 5004
(2007/10/02)
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- CERIC TRIHYDROXY HYDROPEROXIDE Ce(OH)3O2H, A REGENERABLE, MILD, AND A VERSATILE REAGENT FOR THE OXIDATION OF ORGANIC COMPOUNDS.
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Ceric trihydroxy hydroperoxide an easily prepared, a quite stable, and a regenerable oxidant has been used for the oxidation of different organic compounds in dry benzene.
- Firouzabadi, H.,Iranpoor, N.
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p. 875 - 882
(2007/10/02)
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- Benzocyclobutenes. Part 7. Synthesis and X-ray Crystal Structure of Cyclobutaphenanthrene-1,2-dione and the Synthesis of Hexabenzotriphenylene
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Photocycloaddition of tetrachloroethene to phenanthrene gives 1,1,2,2-tetrachloro-1,2,2a,10b-tetrahydrocyclobutaphenanthrene.Treatment of this compound with N-bromosuccinimide gives the corresponding tetrachlorodihydrocyclobutaphenanthrene which can be hydrolysed to cyclobutaphenanthrene-1,2-dione.The 1H and 13C n.m.r. spectra and X-ray molecular structure of the dione have been determined.Flash-vacuum pyrolysis of the dione gives a low yield of hexabenzotriphenylene.
- Hacker, Nigel P.,McOmie, John F. W.,Meunier-Piret, Jacqueline,Meerssche, Maurice Van
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