19301-35-0Relevant articles and documents
Synthesis of new 5-substitutedbenzo[b]thiophene derivatives
Perez-Silanes,Martinez-Esparza,Oficialdegui,Villanueva,Orus,Monge
, p. 1025 - 1030 (2001)
Previous works of our group have dealt with the synthesis of 1-(aryl)-3-[4-(aryl)piperazin-1-yl]propane derivatives in the search for new and efficient antidepressants with a dual mode of action: serotonin reuptake inhibition and 5-HT1A receptor afinity [1-4]. From these studies we concluded that the 3-[4-(aryl)piperazin-1-yl]-l-(benzo[b]thiophen-3-yl)propane derivatives led to the best results. The continuation of this research project required the preparation of some new 3-acyl-5-substituted benzo[b]thiophenes with a wide variety of substituents at the 5 position, ranging from nitro to hydroxyl derivatives. To obtain these derivatives we acylated the corresponding 5-substituted benzo[b]thiophenes when it was possible.
Synthesis and studies on spectroscopic as well as electron donating properties of the two alkoxy benzo[b]thiophenes
Misra,Ganguly,Kamila,Basu,De
, p. 2795 - 2808 (2001)
Synthesis, characterization, steady state and time resolved, using time correlated single photon counting as well as laser flash photolysis techniques, spectroscopic investigations were made for two alkoxy benzo[b]thiophene molecules: 5-methoxy benzo[b]thiophene (5MBT) and 5-methoxymethyl benzo[b]thiophene (5MMBT). In both non-polar n-heptane (NH) and polar acetonitrile (ACN) solvents and at ambient temperature the electronic absorption spectra of these thiophenes exhibit different band systems whose assignments were made from the measurements of the steady state excitation polarization spectra. Steady state fluorescence spectra of these molecules in the different polarity solvents show the presence of non-specific interactions. From the redox properties of the benzothiophenes, measured by cyclic voltammetry, their electron donating properties were observed in the presence of the well-known electron acceptor 9cyanoanthracene (9CNA). Further, detailed studies by laser flash photolysis techniques show that ion-recombination mechanism predominates after the initial excitation of the acceptor moiety using the third harmonic of Nd:YAG laser. This recombination together with the external heavy atom effect (the donor containing 'sulphur' atom) appears to be responsible for the formation of the triplet of the monomeric acceptor 9CNA. From the steady state experiments it is shown that both in non-polar NH and highly polar ACN the quenching in the fluorescence emission of 9CNA in the presence of the benzothiophene donors is brought about primarily by the external heavy atom effect and in ACN, although the presence of the photoinduced ET reaction is confirmed, this process seems, from the observed bimolecular dynamic quenching rate, kq, to be significantly masked by the external heavy atom effect.
Palladium-Catalyzed Hydroxylation of Aryl Halides with Boric Acid
Song, Zhi-Qiang,Wang, Dong-Hui
supporting information, p. 8470 - 8474 (2020/11/18)
Boric acid, B(OH)3, is proved to be an efficient hydroxide reagent in converting (hetero)aryl halides to the corresponding phenols with a Pd catalyst under mild conditions. Various phenol products were obtained in good to excellent yields. This transformation tolerates a broad range of functional groups and molecules, including base-sensitive substituents and complicated pharmaceutical (hetero)aryl halide molecules.
New heteroaryl carbamates: Synthesis and biological screening in vitro and in mammalian cells of wild-type and mutant HIV-protease inhibitors
Tramutola, Francesco,Armentano, Maria Francesca,Berti, Federico,Chiummiento, Lucia,Lupattelli, Paolo,D'Orsi, Rosarita,Miglionico, Rocchina,Milella, Luigi,Bisaccia, Faustino,Funicello, Maria
, p. 1863 - 1870 (2019/03/27)
New heteroaryl HIV-protease inhibitors bearing a carbamoyl spacer were synthesized in few steps and high yield, from commercially available homochiral epoxides. Different substitution patterns were introduced onto a given isopropanoyl-sulfonamide core that can have either H or benzyl group. The in vitro inhibition activity against recombinant protease showed a general beneficial effect of both carbamoyl moiety and the benzyl group, ranging the IC50 values between 11 and 0.6 nM. In particular, benzofuryl and indolyl derivatives showed IC50 values among the best for such structurally simple inhibitors. Docking analysis allowed to identify the favorable situation of such derivatives in terms of number of interactions in the active site, supporting the experimental results. The inhibition activity was also confirmed in HEK293 mammalian cells and was maintained against protease mutants. Furthermore, the metabolic stability was comparable with that of the commercially available inhibitors.
