- Construction of Indole Structure on Pyrroloindolines via AgNTf2-Mediated Amination/Cyclization Cascade: Application to Total Synthesis of (+)-Pestalazine B
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An N-linked indole structure was constructed on the 3a-position of pyrroloindoline derivatives via a cascade process involving silver-mediated amination of bromopyrroloindolines with 2-ethynylanilines with subsequent 5-endo-dig cyclization. In this reaction, AgNTf2 was used as a tandem reagent, which activated the bromo group as a σ-Lewis acid and the alkyne moiety as a π-Lewis acid. Switching from the initial step to the second step was conducted by controlling the temperature. This protocol was applied to the synthesis of various pyrroloindolines, α-carboline, and furoindolines and the total synthesis of a dimeric indole alkaloid, (+)-pestalazine B.
- Hakamata, Hiroyuki,Ueda, Hirofumi,Tokuyama, Hidetoshi
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supporting information
p. 4205 - 4209
(2019/06/17)
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- A catalytic intramolecular nitrene insertion into a copper(i)-N-heterocyclic carbene bond yielding fused nitrogen heterocycles
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N-(2-Azidophenyl)azolium salts were easily prepared and reacted with copper(i) under conditions allowing the formation of NHC complexes. Under these conditions, the formation of benzimidazo-fused heterocycles occurred under catalytic, efficient and very mild conditions. This reaction is proposed to proceed via dinitrogen elimination and imido/nitrene-NHC cyclization.
- Fauché, Kévin,Nauton, Lionel,Jouffret, Laurent,Cisnetti, Federico,Gautier, Arnaud
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supporting information
p. 2402 - 2405
(2017/02/23)
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- NOVEL SUBSTITUTED CONDENSED PYRIMIDINE COMPOUNDS
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Novel substituted condensed pyrimidine compounds of general formula (I) in which the chemical groupings, substituents and indices are as defined in the description, and to their use as medicaments, in particular as medicaments for the treatment of conditions and diseases that can be treated by inhibition of the PDE4 enzyme.
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Page/Page column 28; 29
(2015/02/25)
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- The synthesis and biological testing of bacilysin analogues
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A series of compounds based on the structure of bacilysin were synthesised and tested for antibacterial activity. The key steps in the syntheses are the coupling of an iodide to a diketopiperazine (DKP) and mono-lactim ether scaffold, respectively. The diastereoselectivity of the coupling reactions was dependant on the scaffold, with selectivity for DKP of about 4:1 and mono-lactim ether exceeding 98:2. Subsequent elaboration of the compounds to give open chain dipeptides and DKPs that mimic the structure of bacilysin but substitute the epoxy ketone for a saturated or unsaturated ketone is described. Overall yield from coupling to final product was between 5 and 21 %, with the yield of the saturated products notably higher. The open chain dipeptides demonstrated moderate antibacterial and antifungal activity.
- Robertson, Keith,Murphy, Cormac D.,Paradisi, Francesca
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p. 1157 - 1168
(2013/11/06)
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- Cysteine prodrugs to treat schizophrenia and drug addiction
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The present invention provides cysteine prodrugs for the treatment of schizophrenia and drug addiction. The invention further encompasses pharmaceutical compositions containing prodrugs and methods of using the prodrugs and compositions for treatment of schizophrenia and drug addiction.
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Page/Page column 18-19
(2010/12/29)
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- CYSTEINE AND CYSTINE PRODRUGS TO TREAT SCHIZOPHRENIA AND REDUCE DRUG CRAVINGS
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The present invention provides cysteine and cystine prodrugs for the treatment of schizophrenia and drug addiction. The invention further encompasses pharmaceutical compositions containing prodrugs and methods of using the prodrugs and compositions for treatment of schizophrenia and drug addiction.
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Page/Page column 34
(2009/10/09)
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- Alternative route to metal halide free ionic liquids
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An alternative synthetic route to metal halide free ionic liquids using trialkyloxonium salt is proposed. Utility of this synthetic route has been demonstrated by preparing 1-ethyl-3-methylimidazolium tetrafluoroborate ionic liquid through the reaction be
- Takao, Koichiro,Ikeda, Yasuhisa
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p. 682 - 683
(2008/12/21)
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- Cytosporone E: Racemic synthesis and preliminary antibacterial testing
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The antibiotic cytosporone E (isolated from the broth of the endophytic fungi CR 200 (Cytospora sp.) and CR 146 (Diaporthe sp.)) was synthesized as a racemic mixture. The key step in the synthesis is the Meyers ortho-alkylation of a chiral aromatic oxazoline. Preliminary antibiotic activity shows antibiosis against Gram-positive bacteria but not Gram-negative bacteria as previously reported.
- Hall, Jeffrey D.,Duncan-Gould, Nathan W.,Siddiqi, Nasar A.,Kelly, Jennifer N.,Hoeferlin, L. Alexis,Morrison, Susan J.,Wyatt, Justin K.
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p. 1409 - 1413
(2007/10/03)
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- Method of treating a patient having precancerous lesions with phenyl purinone derivatives
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Derivatives of Phenyl Purinone are useful for the treatment of patients having precancerous lesions. These compounds are also useful to inhibit growth of neoplastic cells.
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- Process for preparing diphenylamines
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A process is described for preparing diphenylamines of the formula STR1 by oxybromination of a phenol ether compound using elemental bromine in the presence of hydrogen peroxide and of a catalyst to give a brominated phenol ether compound which is subsequently reacted with a formanilide compound to give the compound of the formula (1). The oxybromination reaction is a regioselective, environmentally friendly and cost-efffective method of preparing brominated aromatic compounds. The diphenylamines of the formula (1) are industrially useful intermediates for the production, for example of dyes, and in particular of color formers of the fluoran type for pressure- or heat-sensitive recording systems.
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- Conversion of 7-Methoxy-3,4-dihydro-2H-1-benzopyran-2-one into the corresponding dimethyl ortho ester
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7-Methoxy-3,4-dihydro-2H-1-benzopyran-2-one 2 was converted into 3-(2'-tert-butyldimethylsilyloxy-4'-methoxyphenyl)-N-methyl-N-phenylpropanamide 25 and reaction of this with methyl trifluoromethanesulfonate, followed by reaction with sodium methoxide, gave 2,2,7-trimethoxy-2H- 1-benzopyran 1a in 55% overall yield from 25. A similar methylation/methoxide sequence using 3-(2'-benzyloxy-4-methoxyphenyl)-N-methyl-N-phenylpropanamide 18 gave a mixture which contained trimethyl 3-(2'-benzyloxy-4'-methoxyphenyl)orthopropanoate 20a and reaction of this mixture with a solution of sodium in tert-butanol gave a product in which 2,2,7-trimethoxy-2H-1-benzopyran 1a was detected, but not isolable.
- Bourke, David G.,Collins, David J.
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p. 3863 - 3878
(2007/10/03)
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- Propenals substituted with a dithiane ring and processes for the preparation of these propenals
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Propenals of formula: STR1 in which formula R is H or a C1 -C4 thioalkyl radical, the dithiane ring being at the cis position in relation to the aldehyde function when R is H and at the trans position when R is a thioalkyl radical. The invention also relates to two processes for the preparation of these propenals.
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- 2-Substituted purinone having phosphodiesterase inhibitory activity
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This invention relates to phenylpurinone derivatives which have bronchodilator and anti-allergic activities. A compound of the invention is 2-(2-propoxy-5-chlorophenyl)purin-6-one.
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- Lactones. 3. A comparison of the basicities of lactones and esters
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The basicity of lactones and esters toward triethyloxonium ion was studied via NMR spectroscopy. The equilibrium constants were and the order of decreasing basicity was found to be δ-valerolactone > γ-butyrelactone > diethyl carbonate > ethyl acetate > ethyl propionate. The rates of reaction were parallel to the equilibrium constants. The origin of the differences in basicity was via ab initio calculations of structures and energies of ions formed by adding H+ or CH3+ to methyl acetate. The calculated proton affinity of the Z ester rotamer agreed with the experimental data and was found to be considerably smaller than that for the E rotamer. The relative energies of the four ions that could be formed by adding a proton to methyl acetate were related to the orientation of the dipole components at oxygen. The methyl cation affinities of the methyl acetate conformers were found to parallel the proton affinities and gave the same preferred direction of addition. The proton affinity of valerolactone was calculated to be greater than that for butyrolactone in good accord with the experimental results.
- Wiberg, Kenneth B.,Waldron, Boy F.
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p. 7705 - 7709
(2007/10/02)
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- Heterocyclic derivatives of guanidine
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5-Membered, 6-membered and 7-membered heterocyclic derivatives of guanidine having hypoglycemic activity.
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- Diaza-cyclic derivatives of guanidine
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5-Membered 1,3-diazacarbocyclic derivatives of guanidine having hypoglycemic activity.
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- 3(2H)-Isoquinolones therapeutic process
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New 2-substituted-3(2H)-isoquinolones and 2-substituted-3-alkoxyisoquinolines are disclosed. They are orally active hypotensives and peripheral vasodilators with an extended duration of action. Representative embodiments of this invention are 6,7-dimethoxy-2-methyl-1-veratryl-3(2H)-isoquinolone hydrochloride, 2-allyl-6,7-dimethoxy-1-veratryl-3(2H)-isoquinolone hydrochloride, 2-cyclopropyl-6,7-dimethoxy-1-veratryl-3(2H)-isoquinolone hydrochloride, 2-amino-6,7-dimethoxy-1-veratryl-3(2H)-isoquinolone hydrochloride, and 3-ethoxy-6,7-dimethoxy-1-veratrylisoquinoline.
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- Substituted indoles
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Substituted thioindoles and their sulfoxide and sulfone derivatives, useful as cardiac rate lowering agents and for other pharmacological properties, and precursors therefor.
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- Anti-anginal activity of 2-aralkylimino-azepines
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Anti-anginal activity of certain 2-aralkylimino-hexahydro-1-R1 -2H-azepines and pharmaceutical compositions thereof.
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