- 8-Methoxypsoralen-Nucleic Acid Photoreaction. Effect of Methyl Substitution on Pyrone vs. Furan Photoaddition
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We have synthesized a series of 8-methoxypsoralens in which methyl and hydrogen are systematically varied at the 4- and 5'-positions.Analysis of the products resulting from the photoaddition of these four psoralens with the nucleic acid poly(dA-dT) reveals that the product distribution depends on the presence or absence of a 4-methyl substituent.Compounds with the 4-methyl group show an overwhelming preference (ca.98percent) for addition to the furan double bond, while compounds without the 4-methyl show a substantial amount (ca.18percent) of addition to the pyrone double bond.
- Kanne, David,Rapoport, Henry,Hearst, John E.
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- Electronic Finetuning of 8-Methoxy Psoralens by Palladium-Catalyzed Coupling: Acidochromicity and Solvatochromicity
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Differently 5-substituted 8-methoxypsoralens can be synthesized by an efficient synthetic route with various cross-coupling methodologies, such as Suzuki, Sonogashira and Heck reaction. Compared to previously synthesized psoralens, thereby promising daylight absorbing compounds as potentially active agents against certain skin diseases can be readily accessed. Extensive investigations of all synthesized psoralen derivatives reveal fluorescence in the solid state as well as several distinctly emissive derivatives in solution. Donor-substituted psoralens exhibit remarkable photophysical properties, such as high fluorescence quantum yields and pronounced emission solvatochromicity and acidochromicity, which were scrutinized by Lippert–Mataga and Stern–Volmer plots. The results indicate that the compounds exceed the limit of visible light, a significant factor for potential applications as an active agent. In addition, (TD)DFT calculations were performed to elucidate the underlying electronic structure and to assign experimentally obtained data.
- Geenen, Sarah R.,Presser, Lysander,H?lzel, Torsten,Ganter, Christian,Müller, Thomas J. J.
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supporting information
p. 8064 - 8075
(2020/06/02)
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- A Pincer Ruthenium Complex for Regioselective C-H Silylation of Heteroarenes
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A pincer Ru(II) catalyst for the highly efficient undirected silylation of O- and S-heteroarenes with (TMSO)2MeSiH and Et3SiH is described, producing heteroarylsilanes with exclusive C2-regioselectivity, good functional-group tolerance, and high turnover numbers (up to 1960). The synthetic utility of the silylated products is demonstrated by Pd-catalyzed Hiyama-Denmark cross-coupling under mild conditions. One-pot, two-step silylation and coupling procedures have been also developed.
- Fang, Huaquan,Guo, Le,Zhang, Yuxuan,Yao, Wubing,Huang, Zheng
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supporting information
p. 5624 - 5627
(2016/11/17)
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- METHODS FOR SYNTHESIS OF PSORALEN DERIVATIVES
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Methods for the synthesis of psoralen derivatives are provided. In one embodiment, the method may include acetylating a compound of formula (II) to form a compound of formula (III), subjecting the compound of formula (III) to a Fries rearrangement to form a compound of formula (IV), and subjecting the compound of formula (IV) to cyclization, reduction and aromatization, to form a compound having the following formula (I):
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- Synthesis and evaluation of linear furanocoumarins as potential anti-breast and anti-prostate cancer agents
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A series of 22 furanocoumarin derivatives were synthesized and evaluated for cytotoxicity against breast cancer (MCF-7 and MDA-MB-231) and prostate cancer (PC-3) cell lines along with normal cell line. Several analogs were synthesized by replacing prenyl moiety with alkyl, aromatic, and heteroaromatic functionality to study the structure-activity relationship. Compounds 20 and 22 with adamantoylamino, diprenylamino and substituted benzene sulfonamide substituents showed potent antiproliferative activity in MCF-7 cell line with IC50 values of 0.48 and 0.53 μM, respectively. Both the compounds showed higher IC50 value in MCF-10A cell lines indicating nontoxicity in normal cell lines.
- Chauthe, Siddheshwar K.,Mahajan, Shivani,Rachamalla, Mahesh,Tikoo, Kulbhushan,Singh, Inder P.
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p. 2476 - 2484
(2015/02/19)
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- CINAMIC COMPOUNDS AND DERIVATIVES THEREFROM FOR THE INHIBITION OF HISTONE DEACETYLASE
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The invention relates to a compound represented by the following formula (I): and pharmaceutically acceptable salts, stereoisomers, enantiomers, prodrugs and solvates thereof. The compounds are useful as an agent for enhancing the neurite outgrowth and preventing or treating of diseases associated with HDAC in particular, tumor or cell proliferative diseases. In particular, the compounds of the invention can be used as an agent for anti-cancer, anti-diabetic, and anti-neurodegenerative diseases such as Alzheimer's disease, Huntington's disease, Spinocerebellar Ataxias (SCA), and human spinal muscular atrophy (SMA).
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Page/Page column 22-23
(2010/10/19)
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- Cinamic compounds and derivatives therefrom for the inhibition of histone deacetylase
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The invention relates to a compound represented by the following formula (I): and pharmaceutically acceptable salts, stereoisomers, enantiomers, prodrugs and solvates thereof. The compounds are useful as an agent for enhancing the neurite outgrowth and preventing or treating of diseases associated with HDAC in particular, tumor or cell proliferative diseases. In particular, the compounds of the invention can be used as an agent for anti-cancer, anti-diabetic, and anti-neurodegenerative diseases such as Alzheimer's disease, Huntington's disease, Spinocerebellar Ataxias (SCA), and human spinal muscular atrophy (SMA).
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Page/Page column 44-45
(2010/10/19)
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- Reactions of psoralen radical cations with biological substratest
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The reactions of several psoralen and coumarin radical cations with biological substrates such as nucleotides, amino acids and alkenes that serve as models for unsaturated fatty acids have been examined. The radical cations were generated by laser photoionization of the parent psoralen or coumarin in aqueous buffer in most cases. Easily oxidized substrates such as tyrosine, tryptophan and guanosine monophosphate react with the 8-methoxypsoralen and several methoxy-substituted coumarin radical cations with rate constants in excess of 2 × 109 M-1 s-1. In each case reaction occurs via electron transfer, as demonstrated by the observation of quencher-derived radical cations or radicals by transient absorption spectroscopy. For other substrates such as histidine, methionine and adenosine monophosphate the measured rate constants are significantly slower and vary with the oxidation potential of both the parent psoralen or coumarin and the quencher, again indicative of electron transfer reactivity. Most of the alkenes studied also react with the psoralen or coumarin radical cations via electron transfer, although there is some evidence for addition for linoleic acid. Product studies carried out using both lamp and laser irradiation in the presence of deoxyguanosine as a radical cation trap lead to the formation of characteristic base-derived Type-I (electron transfer) products. This lends support to our previous hypothesis that photoionization occurs via a monophotonic process and is thus relevant to conditions used in clinical phototherapeutic applications of psoralens. The results demonstrate the relevance of electron transfer chemistry to the use of psoralens and related compounds as photoactivated drugs.
- Wood, Paul D.,Mnyusiwalla, Anisa,Chen, Lie,Johnston, Linda J.
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p. 155 - 162
(2007/10/03)
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- Anionic [4+2] cycloaddition strategy to linear furocoumarins: Synthesis of 8 methoxypsoralen and its isoster
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The surfoxide esters 14 and 20d are successfully annulated with bicyclic enone 8 in the presence of (t)BuOLi to provide the pentacyclic ketones 9a and 21a respectively in good yields (≤70%). Flash vacuum pyrolysis of O-methyl derivatives 9b and 21b at - 5000 C/. 1 mm provide furoindacenones 16b and 22b respectively, which in turn are convertible to furocoumarins 1 and 3.
- Mal, Dipakranjan,Bandhyopadhyay, Mousumi,Datta,Murty, Kadiyala V. S. N.
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p. 7525 - 7538
(2007/10/03)
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- A Sequential Anionic Cycloaddition And Thermal Cycloreversion Strategy to Furocoumarins: A Concise Synthesis of Methoxsalen
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The synthesis and utility of unprecedented fluorenofurans 7 and oxa-s-indacenones 8 as key intermediates for synthesis of methoxsalen 1 is described, illustrating a novel synthetic approach to furocoumarins.
- Mal, Dipakranjan,Murty, Kadiyala V. S. N.,Datta, Kalyani
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p. 9617 - 9618
(2007/10/02)
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- Treatment methods for lymes disease and associated debilitating conditions
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A method is provided for treating human patients who have Lymes disease by using a psoralen compound, preferably administered in a dosage of 0.3 to 0.7 mg/kg, and activating same either in vitro or in vivo using electromagnetic radiation of a prescribed activating wavelength. The activation of the psoralen compound in the presence of a blood fraction from a patient suffering from Lymes disease produces a composition which will stimulate an effective immune response to the Lymes disease on the part of the patient.
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- Pharmaceutical composition for oral administration and process for the use thereof
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An orally administrable and stable solution containing as an active ingredient Methoxasalen (8-methoxyfuro-[3',-2':6,7]-coumarin) of the formula STR1 useful in the photochemotherapy of psoriasis, to a process for the preparation thereof and to a process for the use thereof.
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- Treatment methods and vaccines for stimulating an immunological response against retroviruses
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Human Immunodeficiency Virus infections, particularly AIDS, are treated by administering a psoralen compound which is subsequently activated by exposure to electromagnetic radiation (e.g. UVA light) whereby the activated psoralen compound attacks free virus and/or virus infected cells in the blood of the patient. The treated blood when presented to the patient's immune system engenders an effective immune response against the infection. The method has particular utility in the treatment of ARC patients who have depressed immune function.
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- CHROMONES AND COUMARINS FROM SKIMMIA LAUREOLA
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The isolation and characterisation of chromones and coumarins, including the new chromone, skimminin, from S. laureola is reported. - Key Word Index: Skimmia laureola; Rutaceae; chromones; skimminin; coumarins; linear furanocoumarins.
- Razdan, T. K.,Qadri, B.,Harkar, S.,Waight, E. S.
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p. 2063 - 2070
(2007/10/02)
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- A Simple One-step Synthesis of Phenyl Ethers from Phenyl Acetates
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Phenyl acetates when refluxed with alkyl halides in acetone solution in the presence of a crown ether and anhydrous potassium carbonate undergo alkylation yielding phenyl ethers.
- Banerjee, Sunil K.,Gupta, Bishan D.,Singh, Kuber
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p. 815 - 816
(2007/10/02)
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- 8-Methoxypsoralen derivatives
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The invention relates to synthetic processes to produce the known pharmacologically active 8-methoxypsoralen and derivatives thereof. Also disclosed are various novel intermediates utilized in these processes.
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- Process for making ω-chloro-2,3,4-trihydroxyacetophenone
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8-Methoxypsoralen is prepared in six steps from pyrogallol including condensation of pyrogallol with a two-fold excess of chloroacetic acid with boron trifluoride hydrogenation of 6,7-dihydroxy-2,3-dihydrobenzofuran and dehydrogenation of 2,3-dihydroxanthotoxin. Improvements in these three steps lead to a marked overall increase in yield.
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- 8-Methoxypsoralen
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8-Methoxypsoralen is prepared in six steps from pyrogallol including hydrogenation of 6,7-dihydroxy-2,3-dihydrobenzofuran and dehydrogenation of 2,3-dihydroxanthotoxin. Improvements in these two steps lead to a marked overall increase in yield.
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