- Phenotypic Screening of Chemical Libraries Enriched by Molecular Docking to Multiple Targets Selected from Glioblastoma Genomic Data
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Like most solid tumors, glioblastoma multiforme (GBM) harbors multiple overexpressed and mutated genes that affect several signaling pathways. Suppressing tumor growth of solid tumors like GBM without toxicity may be achieved by small molecules that selec
- Aryal, Uma K.,Bailey, Barbara J.,Bum-Erdene, Khuchtumur,Corson, Timothy W.,Fishel, Melissa L.,Lee, Jonathan A.,Liu, Sheng,Meroueh, Samy O.,Pollok, Karen E.,Sishtla, Kamakshi,Wan, Jun,Wells, Clark D.,Xu, David,Zhou, Donghui
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p. 1424 - 1444
(2020/07/15)
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- Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis
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A general and efficient method for heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram scale is reported. The potential application of this new methodology is demonstrated by the total synthesis of (-)-codonopsinine and (+)-centrolobine. Herein it is proposed that selectfluor, unlike a fluorinating reagent, acts as an oxidative quencher and a hydrogen radical acceptor.
- Pandey, Ganesh,Laha, Ramkrishna,Mondal, Pradip Kumar
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p. 9689 - 9692
(2019/08/15)
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- Chemoselective Intramolecular Formal Insertion Reaction of Rh–Nitrenes into an Amide Bond Over C?H Insertion
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The past few decades have witnessed extensive efforts to disclose the unique reactivity of metal–nitrenes, because they could be a powerful synthetic tool for introducing the amine functionality into unactivated chemical bonds. The reactivity of metal–nitrenes, however, is currently mainly confined to aziridination (an insertion into a C=C bond) and C?H amination (an insertion into a C?H bond). Nitrene insertion into an amide C?N bond, however, has not been reported so far. In this work we have developed a rhodium-catalyzed one-nitrogen insertion into amide C?N and sulfonamide S?N bonds. Experimental and theoretical analyses based on density functional theory indicate that the formal amide insertion proceeds via a rhodium-coordinated ammonium ylide formed between the nitrene and the amide nitrogen, followed by acyl group transfer concomitant with C?N bond cleavage. Mechanistic studies have allowed rationalization of the origin of the chemoselectivity observed between the C?H and amide insertion reactions. The methodology presented herein is the first example of an insertion of nitrene into amide bonds and provides facile access to unique diazacyclic systems with an N?N bond linkage.
- Kono, Masato,Harada, Shingo,Nemoto, Tetsuhiro
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supporting information
p. 3119 - 3124
(2019/02/13)
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- Preparation method of polysubstituted pyrrole compound
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The invention discloses a preparation method of a polysubstituted pyrrole compound. The preparation method comprises steps as follows: an alkyne enamine compound is subjected to a cyclization reactionunder the catalytic action of univalent gold, a product
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Paragraph 0052-0055
(2018/09/26)
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- Synthesis of 2-carboxylated aza-ring derivatives through α-monohalogenation/ring-contraction of N-sulfonyl lactams
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2-Carboxylated aza-rings have been synthesized in two steps through a highly selective monohalogenation of N-sulfonylated lactams of various ring sizes (from 5- to 8-membered rings) followed by a ring contraction reaction. The selective monohalogenation of N-sulfonyl lactams has been achieved in modest to excellent yields (9 examples, 39–96%) using N-halogenosuccinimides via the in situ generation of trimethylsilyl ketene aminal derivatives. The so-obtained α-halogeno N-sulfonyl lactams were engaged in a ring opening/ring closing reaction in the presence of various alcohols or anilines under basic conditions affording 2-carboxylated aza-rings, such as azetidine, pyrrolidine or piperidine derivatives in high yields (24 examples, 61–99%).
- Sirindil, Fatih,Miaskiewicz, Solène,Kern, Nicolas,Lalaut, Arno,Felten, Anne-Sophie,Weibel, Jean-Marc,Pale, Patrick,Blanc, Aurélien
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p. 5096 - 5106
(2017/07/28)
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- Highly stereoselective syntheses of proline-derived vicinal amino alcohols through grignard addition onto N-tosylprolinal
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A highly diastereoselective Grignard addition to N-tosyl-l-prolinal has been developed to deliver a variety of proline-derived vicinal amino alcohols in good to excellent yields with high diastereoselectivities. A similar selectivity was also obtained by using N-tosyl-d-prolinal. The methodology has been applied to the synthesis of medicinally important 3-hydroxy-2-phenylpiperidines.
- Chaudhuri, Saikat,Parida, Amarchand,Ghosh, Santanu,Bisai, Alakesh
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p. 215 - 220
(2016/01/20)
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- Gold(I)-Catalyzed N-Desulfonylative Amination versus N-to-O 1,5-Sulfonyl Migration: A Versatile Approach to 1-Azabicycloalkanes
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Valuable 1-azabicycloalkane derivatives have been synthesized through a novel gold(I)-catalyzed desulfonylative cyclization strategy. An ammoniumation reaction of ynones substituted at the 1-position with an N-sulfonyl azacycle took place in the presence of a gold cation by intramolecular cyclization of the disubstituted sulfonamide moiety onto the triple bond. Depending on the size of the heterocyclic ring and substitution of the substrates, two unprecedented forms of nucleophilic attack on the sulfonyl group were exploited, that is, a N-desulfonylation in the presence of an external protic O nucleophile (37–87 %, 10 examples) and a unique N-to-O 1,5-sulfonyl migration (60–98 %, 9 examples).
- Miaskiewicz, Solène,Gaillard, Boris,Kern, Nicolas,Weibel, Jean-Marc,Pale, Patrick,Blanc, Aurélien
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supporting information
p. 9088 - 9092
(2016/07/26)
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- Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides
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Mechanistic evidence observed in Hofmann-L?ffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity. (Chemical Equation Presented).
- Paz, Nieves R.,Rodríguez-Sosa, Dionisio,Valdés, Haydee,Marticorena, Ricardo,Melián, Daniel,Copano, M. Belén,González, Concepción C.,Herrera, Antonio J.
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p. 2370 - 2373
(2015/06/02)
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- NAlkylation of tosylamides using esters as primary and tertiary alkyl sources: Mediated by hydrosilanes activated by a ruthenium catalyst
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Select your group: Either a primary or tertiary alkyl group can be selectively introduced onto the nitrogen atom of tosylamides in a ruthenium-catalyzed reaction employing hydrosilanes through a judicious choice in the esters that serve as the alkyl source (see scheme; Ts= 4-toluenesulfonyl). These N-alkylation reactions are useful for construction of naturally occurring azacyclic skeletons. Copyright
- Nishikata, Takashi,Nagashima, Hideo
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supporting information; experimental part
p. 5363 - 5366
(2012/07/03)
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- Counterion-mediated hydrogen-bonding effects: Mechanistic study of gold(I)-catalyzed enantioselective hydroamination of allenes
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Two of a kind: A new type of counterion-mediated syn-addition mechanism has been presented in gold-catalyzed enantioselective hydroamination reactions with [(R)-binap(AuOPNB)2] (OPNB=para-nitrobenzoate). A combination of both hydrogen bonding and the N-Au interaction efficiently controlled the challenging enantioselectivity of allenes.
- Kim, Ji Hye,Park, Sung-Woo,Park, Sae Rom,Lee, Sungyul,Kang, Eun Joo
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supporting information; experimental part
p. 1982 - 1986
(2011/10/31)
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- Gold(I)-catalyzed enantioselective intramolecular hydroamination of allenes
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The asymmetric intramolecular hydroamination of allenes catalyzed by phosphinegold(I)-bis-p-nitrobenzoate complexes is described. This reaction is applicable to the enantioselective formation of vinyl pyrrolidines and piperidines in 70-99% ee. Copyright
- Lalonde, Rebecca L.,Sherry, Benjamin D.,Kang, Eun Joo,Toste, F. Dean
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p. 2452 - 2453
(2007/10/03)
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- The photochemistry of N-p-toluenesulfonyl peptides: The peptide bond as an electron donor
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The scope of photobiological processes that involve absorbers within a protein matrix may be limited by the vulnerability of the peptide group to attack by highly reactive redox centers consequent upon electronic excitation. We have explored the nature of this vulnerability by undertaking comprehensive product analyses of aqueous photolysates of 12 N-p-toluene-sulfonyl peptides with systematically selected structures. The results indicate that degradation includes a major pathway that is initiated by intramolecular electron transfer in which the peptide bond serves as electron donor, and the data support the likelihood' of a relay process in dipeptide derivatives.
- Hill, Roger R.,Moore, Sharon A.,Roberts, David R.
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p. 1439 - 1446
(2008/02/01)
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- 1-sulfonyl pyrrolidine derivatives
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The present invention is a series of compounds that are derivatives of 1-sulfonyl-pyrrolidine and that demonstrate affinity towards metabotropic glutamate receptors. The invention further relates to medicaments containing these compounds and to a process for their preparation. The compounds possess affinity towards metabotropic glutamate receptors and are therefore useful in the treatment or prevention of acute and/or chronic neurological disorders.
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- Modified tripeptides
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Modified oxytocin-vasopressin di- or tri-peptides wherein an amide group is replaced by a group selected from STR1 --CH2 NH--, --CH2 O--, --CH2 S--, --CH2 SO--, --CH2 SO2 --, --CH2/su
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- REGIOSELECTIVE TRANSFORMATION OF UNSYMMETRICAL BIS(N-NITROSOSULFONAMIDES) LEADING TO OPTICALLY ACTIVE CYCLIC IMINO ACID DERIVATIVES FROM L-LYSINE AND L-ORNITHINE
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Chiral cyclic imino acid derivatives were prepared from unsymmetrical bis(N-nitrososulfonamides) of diaminocarboxylic acids, L-lysine and L-ornithine, in good yields through kinetically controlled regioselective N-nitrososulfonamide-sulfonate rearrangement.
- Iwata, Masaaki,Kuzuhara, Hiroyoshi
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p. 1941 - 1942
(2007/10/02)
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- Electroorganic Chemistry. 81. Anodic Oxidation of Sulfonamides and Amidophosphates
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Oxidation peak potentials of sulfonamides and amidophosphates were measured in acetonitrile and compared with the corresponding amides and carbamates.The results showed that the order of easiness of oxidation was amides > carbamates > amidophosphates > sulfonamides.Furthermore, the reaction of silyl enol ethers or trimethyl phosphite with anodically α-methoxylated sulfonamides or amidophosphates has clearly shown that the α-methoxylated compounds are useful starting materials in organic synthesis.For example, optically active L-tryptophan was synthesized from α-methoxylated N-(p-tolylsulfonyl)-L-proline ester.
- Shono, Tatsuya,Matsumura, Yoshihiro,Tsubata, Kenji,Uchida, Kenshi,Kanazawa, Takenobu,Tsuda, Kunio
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p. 3711 - 3716
(2007/10/02)
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- A GENERAL METHOD FOR THE SYNTHESIS OF INDOLES BEARING A VARIETY OF SUBSTITUENTS AT THE β-POSITION, AND ITS APPLICATION TO THE SYNTHESIS OF L-TRYPTOPHAN
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A general synthetic method of β-substituted indoles such as indolacetic acid, tryptamine and L-tryptophan has been exploited utilizing α-methoxylated amides, lactams, a carbamate, and sulfonamides, easily obtainable by an electrochemical method, as key intemediates.
- Shono, Tatsuya,Matsumura, Yoshihiro,Kanazawa, Takenobu
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p. 1259 - 1262
(2007/10/02)
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