3163-27-7Relevant articles and documents
Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor-Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones
Denisov, Dmitry A.,Borisov, Denis D.,Korolev, Victor A.,Novikov, Roman A.,Tomilov, Yury V.
, p. 6174 - 6182 (2019)
A new cascade three-component process for high trans,trans-diastereoselective assembly of five-membered (1-halovinyl)lactones has been developed. The process is based on reactions of substituted methylidenemalonates and cyclopropanedicarboxylates with 3-haloprop-1-ynes in the presence of GaHal3 and involves the intermediate in situ generation of 1,2-zwitterionic gallium complexes with [Ga(L)3]3+[GaX4-]3 composition. Chloro, bromo, and iodo derivatives can be obtained successfully. Mechanistic and stereochemical aspects of the process we developed have been studied and considered in detail.
Identification of pheromone-like compounds in male reproductive organs of the oriental locust Locusta migratoria
Ban, Liping,Napolitano, Elio,Serra, Andrea,Zhou, Xianhong,Iovinella, Immacolata,Pelosi, Paolo
, p. 620 - 624 (2013)
Despite the great economical interest of locusts in agriculture, knowledge on their chemoreception systems is still poor. Phenylacetonitrile is recognised as a pheromone of the desert locust Schistocerca gregaria, triggering gregarization, promoting aggregation and inhibiting courtship. However, in the other major locust species, Locusta migratoria, pheromones have not been reported. We have identified the two isomers of naphthylpropionitrile from the male reproductive organs of L. migratoria. Chemical synthesis has confirmed the identity of the two compounds. Both isomers show significant affinity to CSP91, a protein reported in the testis, but not to three other proteins of the same family (CSP180, CSP540 and CSP884) expressed in female accessory glands. The striking similarity of these compounds with phenylacetonitrile and the unusual nature of such chemicals strongly suggest that naphthylpropionitrile could be pheromones for L. migratoria, while their site of expression and binding activity indicate a role in communication between sexes.
Photodecarboxylation of Substituted Naphthylmethyl Arylacetate Esters: Synthesis of Naphthylarylethanes
Hilborn, James W.,Moya-Barrios, Reinaldo,Thompson, Alison
, p. 11992 - 11999 (2019)
The synthesis of naphthylarylethanes via the photodecarboxylation of naphthylmethyl arylacetate esters is reported where the aryl group is able to stabilize a charge transfer reaction. The reaction proceeds via intramolecular charge transfer from the donor to acceptor, thereby enhancing a pathway to produce, within the solvent cage, the desired diarylethane products. These in-cage naphthylarylethanes are produced in good yields, in a single photochemical step, with the use of cyclohexane as a solvent providing optimal yields.
Antiproliferative activity of diarylnaphthylpyrrolidine derivative via dual target inhibition
Chanda, Debabrata,Dudi, Rajesh Kumar,Fatima, Kaneez,Iqbal, Hina,Khan, Feroz,Kumar, Yogesh,Luqman, Suaib,Mondhe, D. M.,Negi, Arvind S.,Shanker, Karuna,Tabassum, Misbah,Verma, Amit Kumar
, (2020)
Breast cancer is the second leading cause of deaths in women globally. Present communication deals with design and synthesis of a few diarylnaphthyls as possible anti-breast cancer agents. Among the thirteen thirty three representatives with significant antiproliferative activity compounds 23 and 50 were quite efficacious against human breast cancer cells. Compound 50 induced apoptosis in both MCF-7 and MDA-MB-231 cells and exerted S phase and G2/M phase arrest respectively via distinct mechanistic pathways. It showed moderate microtubule destabilization. Further, it exhibited DNA topoisomerase-II inhibition effect in MCF-7 cells. It was well tolerable and found safe up to 300 mg/kg dose in Swiss albino mice. The dual action antiproliferative effect of compound 50 is quite interesting and warrants for future development.
Preparation method of naphthalene ring C marked α .
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Paragraph 0046-0047; 0050; 0056-0057; 0060; 0066-0067; 0070, (2021/10/05)
The invention discloses C labeled α - naphthalene acetic acid preparation method and belongs to the field of radioisotope C labeled compounds. C-labeled α - naphthylacetic acid preparation method, C radioisotope labeling is introduced on a naphthalene ring structure α -naphthol acid, C labeling site is in α-position. The method has the advantages that the reaction raw materials are easily available, the synthesis steps are high in yield, the total yield is more 60%, C marker isotopes are less in use amount, and waste is generated. The marker site α-position on the naphthalene ring is less likely to be metabolized compared to C-labeled branched acetic acid, and the synthesized C-labeled compound provides a better study of α -naphthoic acid in the environment.
Bioisosteric Modification of To042: Synthesis and Evaluation of Promising Use-Dependent Inhibitors of Voltage-Gated Sodium Channels
Milani, Gualtiero,Cavalluzzi, Maria Maddalena,Altamura, Concetta,Santoro, Antonella,Perrone, Mariagrazia,Muraglia, Marilena,Colabufo, Nicola Antonio,Corbo, Filomena,Casalino, Elisabetta,Franchini, Carlo,Pisano, Isabella,Desaphy, Jean-Fran?ois,Carrieri, Antonio,Carocci, Alessia,Lentini, Giovanni
, p. 3588 - 3599 (2021/10/07)
Three analogues of To042, a tocainide-related lead compound recently reported for the treatment of myotonia, were synthesized and evaluated in vitro as skeletal muscle sodium channel blockers possibly endowed with enhanced use-dependent behavior. Patch-clamp experiments on hNav1.4 expressed in HEK293 cells showed that N-[(naphthalen-1-yl)methyl]-4-[(2,6-dimethyl)phenoxy]butan-2-amine, the aryloxyalkyl bioisostere of To042, exerted a higher use-dependent block than To042 thus being able to preferentially block the channels in over-excited membranes while preserving healthy tissue function. It also showed the lowest active transport across BBB according to the results of P-glycoprotein (P-gp) interacting activity evaluation and the highest cytoprotective effect on HeLa cells. Quantum mechanical calculations and dockings gave insights on the most probable conformation of the aryloxyalkyl bioisostere of To042 in solution and the target residues involved in the binding, respectively. Both approaches indicated the conformations that might be adopted in both the unbound and bound state of the ligand. Overall, N-[(naphthalen-1-yl)methyl]-4-[(2,6-dimethyl)phenoxy]butan-2-amine exhibits an interesting toxico-pharmacological profile and deserves further investigation.
A mild method for the replacement of a hydroxyl group by halogen: 2. unified procedure and stereochemical studies
Gati, Wafa,Munyemana, Fran?ois,Colens, Alain,Srour, Aladdin,Dufour, Mathilde,Vardhan Reddy, K. Harsha,Téchy, Brigitte,Rosse, Gérard,Schweiger, Ed,Qiao, Qi,Ghosez, Léon
, (2020/08/19)
N,N-Dimethyl- and N,N-diisopropyl-1-halo-2-methyl-l-propenylamines are readily available reagents for the mild deoxyhalogenation of alcohols and hydroxyacids. In this study we showed that the reactivity of the reagents can be tuned by varying the size of the alkyl groups on the reagents: the replacement of methyl by isopropyl groups led to a significant increase of reactivity. We then described a unified procedure for all deoxyhalogenations using the readily available α-chloroenamines as reagents with (bromination, iodination) or without (chlorination) an alkaline bromide or iodide. Finally, we showed that deoxyhalogenation reactions of secondary alcohols were highly stereospecific and generally occurred with inversion of configuration.
Methylarene-based PAH synthesis via domino cyclization of 1, 1-difluoro-1-alkenes
Fuchibe, Kohei,Takao, Go,Takahashi, Hiroki,Ijima, Shiori,Ichikawa, Junji
, p. 2019 - 2029 (2019/12/23)
Polycyclic aromatic hydrocarbons (PAHs) containing 4-7 benzene rings were synthesized via a methylarene-based protocol. Trimethyl[2-(trifluoromethyl)allyl]silane was electrophilically benzylated with Ar1CH2Br (prepared from Ar1CH3) to afford 2-trifluoromethyl-1-alkenes that were in turn nucleophilically benzylated with Ar2CH2Li (prepared from Ar2CH3) through an SN2-type reaction to produce 1, 1-difluoroethylenes, which are cyclization precursors bearing two 2-arylethyl groups. Magic acid efficiently promoted the domino FriedelCrafts-type cyclization of these precursors, followed by dehydrogenation that enabled the connection among two aryl groups (Ar1 and Ar2) by forming two benzene rings between them, facilitating the synthesis of the desired higher-order PAHs. With the proposed protocol, the combination of even a limited number of methylarenes can yield a variety of PAHs in diverse configurations.
XANTHINE DERIVATIVES AND USES THEREOF AS INHIBITORS OF BROMODOMAINS OF BET PROTEINS
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Page/Page column 30; 32, (2019/05/22)
The present invention relates to a compound having the following formula (I): (I) wherein: - R is a (C1-C6)alkyl group;- R'' is preferably H;- Ar is a (C5-C12)arylene radical;- X1 is -C(=O)- or -SO2-; and- R' is chosen from the group consisting of possibly substituted (C1-C6)alkyl, heteroaryl, (C5-C12)aryl, and (hetero)cycloalkyl groups, or a pharmaceutically acceptable salt and/or tautomeric form thereof, or its racemates, diastereomers or enantiomers.
Promotion of Appel-type reactions by N-heterocyclic carbenes
Hussein, Mohanad A.,Nguyen, Thanh Vinh
supporting information, p. 7962 - 7965 (2019/07/12)
N-Heterocyclic carbenes (NHCs) have been extensively used as a versatile class of catalysts and ligands in organocatalytic and organometallic chemistry. However, there are only a small number of synthetic applications where they act as reagents. Here we demonstrate that NHCs can be used as stoichiometric redox reagents for Appel-type halogenation reactions of alcohols. This new reactivity reveals a fresh and interesting aspect and enriches the chemistry of NHCs in an underexplored area. The potential of performing this chemical transformation at the catalytic level using an NHC-oxide derivative is also investigated.
