13781-67-4Relevant academic research and scientific papers
Synthesis of two novel cysteine-functionalized thiophenes
Cagnoli, Rita,Lanzi, Massimiliano,Mucci, Adele,Parenti, Francesca,Schenetti, Luisa
, p. 267 - 271 (2005)
The synthetic approach to methyl N-(tert-butoxycarbonyl)-S-(3-thienyl)-L- cysteinate (1) and methyl N-(tert-butoxycarbonyl)-S-[2-(3-thienyl)ethyl]-L- cysteinate (2) through tosylate intermediates is reported and discussed. These compounds, which combine the properties of the cysteine side-chain with those of the thiophene ring represent both potential bioactive molecules and interesting synthons for the development of new materials.
Preparation of a New Spirobi[thieno[2,3- c ]pyran] and Its Selective Mono- and Dimetalation: Application for the Preparation of Soluble Conjugated Oligothiophenes and Pyrene Derivatives
Dhayalan, Vasudevan,Alca?iz, Fernando Rabasa,Werner, Veronika,Karaghiosoff, Konstantin,Knochel, Paul
, p. 3972 - 3982 (2015)
3-Thienylacetic acid was converted in six steps into a new spirobi[thieno[2,3-c]pyran] (overall yield: 52%). The spirobi[thieno[2,3-c]pyran] was selectively mono- or dimetalated with butyllithium and then transmetalated with zinc chloride; cross-coupling reaction with various aryl or heteroaryl bromides, including bromo-oligothiophenes, acid chlorides, and 1-bromopyrene, produced the corresponding spiro derivatives in high yields.
Synthesis and evaluation of 4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran] analogues against both active and dormant Mycobacterium tuberculosis
Alluri, Kiran Kumar,Reshma, Rudraraju Srilakshmi,Suraparaju, Raghuram,Gottapu, Suryanarayana,Sriram, Dharmarajan
, p. 1462 - 1469 (2018)
Need for new drugs to fight against tuberculosis (TB) is increasing day by day. In the present work we have taken a spiro compound (GSK 2200150A) reported by GSK as a lead and we modified the structure of the lead to study the antitubercular activity. For structure activity profiling twenty-one molecules have been synthesized, characterized and evaluated for their antimycobacterial potency against both active and dormant TB. Compound 06, 1-((4-methoxyphenyl)sulfonyl)-4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran] was found to be the most potent compound (MIC: 8.23 μM) in active TB and was less effective than the lead but more potent than standard first line drug ethambutol. It was also found to be more efficacious than Isoniazid and Rifampicin and equipotent as Moxifloxacin against dormant Mycobacterium tuberculosis (MTB). Compound 06 also showed good inhibitory potential against over expressed latent MTB enzyme lysine ε-amino transferase with an IC50 of 1.04 ± 0.32 μM. This compound is a good candidate for drug development owing to potential against both active and dormant stages of MTB.
HETEROARYL COMPOUNDS USEFUL AS INHIBITORS OF SUMO ACTIVATING ENZYME
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Paragraph 00367, (2016/01/25)
Disclosed are chemical entities which are compounds of formula (I); or pharmaceutically acceptable salts thereof; wherein Y, Ra, Ra', Rb, Rc, X1, X2, X3, Rd, Z1, and Z2 have the values described herein and stereochemical configurations depicted at asterisked positions indicate absolute stereochemistry. Chemical entities according to the disclosure can be useful as inhibitors of Sumo Activating Enzyme (SAE). Further provided are pharmaceutical compositions comprising a compound of the disclosure and methods of using the compositions in the treatment of proliferative, inflammatory, cardiovascular, and neurodegenerative diseases or disorders.
Synthesis of an ORL-1 Receptor Antagonist via a Radical Bromination and Deoxyfluorination to Afford a gem-Difluorospirocycle
Debaillie, Amy C.,Jones, Chauncey D.,Magnus, Nicholas A.,Mateos, Carlos,Torrado, Alicia,Wepsiec, James P.,Tokala, Ramachandar,Raje, Prasad
, p. 1568 - 1575 (2015/11/28)
The development of a synthesis of an ORL-1 receptor antagonist is described. The key process improvements in the synthetic sequence include a multikilogram bromination process and the development of a convergent coupling strategy. The process improvements resulted in the production of the active pharmaceutical ingredient (API) on a multikilogram scale.
α-Alkylidene-γ-butyrolactone synthesis via one-pot C-H insertion/olefination: substrate scope and the total synthesis of (±)-cedarmycins A and B
Lloyd, Matthew G.,D'Acunto, Mariantonietta,Taylor, Richard J.K.,Unsworth, William P.
, p. 7107 - 7123 (2015/02/19)
Abstract A system for the synthesis of α-alkylidene-γ-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of α-diazo-α-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (±)-cedarmycins A and B is also described.
Reduction of aromatic and aliphatic esters using the reducing systems MoO2(acac)2 or V(O)(OiPr)3 in combination with 1,1,3,3-tetramethyldisiloxane
Pehlivan, Leyla,Metay, Estelle,Laval, Stephane,Dayoub, Wissam,Delbrayelle, Dominique,Mignani, Gerard,Lemaire, Marc
experimental part, p. 7400 - 7406 (2012/01/06)
An efficient reduction of aromatic and aliphatic esters with 1,1,3,3-tetramethyldisiloxane in combination with [MoO2(acac) 2] or [V(O)(OiPr)3] is reported. In the former system, the presence of triphenylphosphane oxide allows high conversion and good isolated yield to be reached. For the latter system, no ligand is necessary to obtain the corresponding alcohols with similar results. 1,1,3,3-Tetramethyldisiloxane in association with [MoO2(acac)2] or [V(O)(OiPr)3] was found to efficiently reduce aliphatic and aromatic esters. Copyright
BENZOXEPIN PI3K INHIBITOR COMPOUNDS AND METHODS OF USE
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Page/Page column 148, (2011/04/19)
Benzoxepin compounds of Formula I, and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, wherein: Z1 is CR1 or N; Z2 is CR2 or N; Z3 is CR3 or N; Z4 is CR4 or N; and where (i) X1 is N and X2 is S, (ii) X1 is S and X2 is N, (iii) X1 is CR7 and X2 is S, (iv) X1 is S and X2 is CR7; (v) X1 is NR8 and X2 is N, (vi) X1 is N and X2 is NR8, (vii) X1 is CR7 and X2 is O, (viii) X1 is O and X2 is CR7, (ix) X1 is CR7 and X2 is C(R7)2, (x) X1 is C(R7)2 and X2 is CR7; (xi) X1 is N and X2 is O, or (xii) X1 is O and X2 is N, are useful for inhibiting lipid kinases including p110 alpha and other isoforms of PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.
Novel, one-pot procedure for the synthesis of 2-arylethanol derivatives
Schlaeger, Torsten,Oberdorf, Christoph,Tewes, Bastian,Wuensch, Bernhard
, p. 1793 - 1797 (2008/12/22)
An efficient one-pot synthesis of 2-arylethanol derivatives using ethylene sulfate as a C2 building block is described. High yields are obtained upon trapping of aryllithium intermediates generated by halogen-metal exchange or directed metalation with ethylene sulfate. The resulting heteroaryl or phenylethanol derivatives represent versatile building blocks for the synthesis of annulated pyran derivatives by oxa-Pictet-Spengler reaction.
Triflic anhydride-promoted cyclization of sulfides: A convenient synthesis of fused sulfur heterocycles
Shevchenko, Nikolay E.,Nenajdenko, Valentine G.,Balenkova, Elizabeth S.
, p. 1191 - 1200 (2007/10/03)
A new approach to the synthesis of annulated sulfur heterocycles based on triflic anhydride-promoted cyclization of the hetaryl(aryl) containing alkyl sulfides was elaborated. Smooth demethylation of initially formed cyclic sulfonium salts by treatment with triethylamine afforded a number of five-, six- and seven-membered fused sulfur heterocycles. Unexpected ring opening took place in the reaction of diethylamine with 5-membered sulfonium salts.
