40032-76-6Relevant articles and documents
Discovery of N-Substituted (2-Phenylcyclopropyl)methylamines as Functionally Selective Serotonin 2C Receptor Agonists for Potential Use as Antipsychotic Medications
Zhang, Guiping,Cheng, Jianjun,McCorvy, John D.,Lorello, Paul J.,Caldarone, Barbara J.,Roth, Bryan L.,Kozikowski, Alan P.
, p. 6273 - 6288 (2017)
A series of N-substituted (2-phenylcyclopropyl)methylamines were designed and synthesized, with the aim of finding serotonin 2C (5-HT2C)-selective agonists with a preference for Gq signaling. A number of these compounds exhibit 5-HT2C selectivity with a preference for Gq-mediated signaling compared with β-arrestin recruitment. Furthermore, the N-methyl compound (+)-15a, which displayed an EC50 of 23 nM in the calcium flux assay while showing no β-arrestin recruitment activity, is the most functionally selective 5-HT2C agonist reported to date. The N-benzyl compound (+)-19, which showed an EC50 of 24 nM at the 5-HT2C receptor, is fully selective over the 5-HT2B receptor. In an amphetamine-induced hyperactivity model, compound (+)-19 showed significant antipsychotic-drug-like activity. These novel compounds shed light on the role of functional selectivity at the 5-HT2C receptor with respect to antipsychotic activity.
Synthesis of Poly(3-substituted thiophene)s of Remarkably High Solubility in Hydrocarbon via Nickel-Catalyzed Deprotonative Cross-Coupling Polycondensation
Fujita, Keisuke,Sumino, Yugo,Ide, Kenji,Tamba, Shunsuke,Shono, Keisuke,Shen, Jian,Nishino, Takashi,Mori, Atsunori,Yasuda, Takeshi
, p. 1259 - 1269 (2016)
Polythiophenes bearing a siloxane moiety in a substituent at the 3-position are prepared by deprotonative polycondensation of 2-bromo-3-substituted-thiophene with a bulky magnesium amide chloromagnesium 2,2,6,6-tetramethylpiperidine-1-yl lithium chloride salt (TMPMgCl·LiCl) catalyzed by a nickel complex. Deprotonation takes place at 60 °C for 1 h to form the corresponding thiophene magnesium species, which is subjected to the polymerization by addition of 0.1-5 mol % NiCl2(PPh3)IPr (IPr: 1,3-bis(2,6-diisopropylphenyl)imidazole-2-yl). Polymerization proceeds in a highly regioregular manner, and the molecular weight of the thus-obtained polymer is controllable by the ratio of monomer feed/catalyst loading to indicate Mn of up to 280 000 with narrow molecular weight distribution. Chlorothiophenes are also found to induce polymerization in a deprotonative manner with TMPMgCl·LiCl or nBuLi (the Murahashi coupling polymerization). The obtained polymers bearing a siloxane moiety in the substituent is revealed to be dissolved in a hydrocarbon allowing formation of thin film from hexane.
Synthesis, Structure, and Dynamics of Chiral Eight-Membered Cyclic Molecules with Thienylene and Cyclopropylene Units Alternately Connected
Ishihara, Yumi,Miura, Tomoya,Moritani, Shunsuke,Murakami, Masahiro,Nagata, Yuuya,Nakamuro, Takayuki
supporting information, (2022/01/22)
A rhodium(II)-catalyzed asymmetric cyclooligomerization of bifunctional monomers possessing triazolyl and vinyl groups at 2,3- and 3,4-positions on the thiophene ring is studied. Structurally interesting cyclic dimers in which thienylene and cyclopropylene units are alternately connected are obtained as the major components. The eight-membered rings in the center are non-planar and adopt a tub-shaped conformation. We also observe the phenomenon of racemization caused by a tub-to-tub ring-flipping, the activation energy of which is determined as 108 kJ mol?1 by electronic circular dichroism spectra measurement.
One-Pot Regiodirected Annulations for the Rapid Synthesis of ?-Extended Oligomers
Bianchi, Gabriele,Botta, Chiara,Calcagno, Giuseppe,Etkind, Samuel I.,Nitti, Andrea,Osw, Peshawa,Pasini, Dario,Po, Riccardo,Swager, Timothy M.
supporting information, p. 3263 - 3267 (2020/04/21)
We demonstrate the broad applicability of the annulation protocol combining, in one pot, a direct arylation and cross aldol condensation for the straightforward synthesis at gram-scale of ?-extended thiophene-based scaffolds. The regiospecific direct arylation drives the subsequent cross-aldol condensation proceed under the same basic conditions, and the overall protocol has broad applicability in the synthesis of extended aromatics wherein the thiophene ring is annulated with furans, pyridines, indoles, benzothiophenes, and benzofurans. These scaffolds can be further elaborated into ?-extended, highly fluorescent oligomers with a central deficient benzothiadiazole unit with up to nine aromatic rings through coupling reactions.
Fine-tuning the solid-state ordering and thermoelectric performance of regioregular P3HT analogues by sequential oxygen-substitution of carbon atoms along the alkyl side chains
Chen, Liangjun,Liu, Wei,Yan, Yonggao,Su, Xianli,Xiao, Shengqiang,Lu, Xinhui,Uher, Ctirad,Tang, Xinfeng
, p. 2333 - 2344 (2019/03/05)
Conjugated polymers in thin films tend to orient their backbones with respect to substrates through self-assembly when processed from a solution. The molecular packing orientation and crystallinity of polymer crystals have been found to play a critical role in terms of their electrical performance. Taking advantage of the shorter bond length and the smaller rotation energy of the CH2-O bond than those of the CH2-CH2 bond in an alkyl chain, a side-chain engineering strategy is reported, which involves sequential oxygen-substitution of the carbon atoms from the γ position outwards along the hexyls in regioregular poly(3-hexylthiophene) (RR-P3HT). The subtle disparity between the CH2-O and CH2-CH2 bonds is found to enable fine tuning of the solid-state organization of the corresponding RR-P3HT analogues, namely poly(3-(2-propoxyethyl)thiophene) (P3POET), poly(3-(3-ethoxypropyl)thiophene) (P3EOPT) and poly(3-(4-methoxybutyl)thiophene) (P3MOBT). The evolution of film microstructures is observed when doping with FeCl3 in nitromethane at room temperature, and so is their thermoelectric performance. The highest power factor of 19 μW m-1 K-2 was observed for the doped P3POET film, which presents a dominant edge-on orientation with the strongest crystallinity and the closest π-π stacking. At the doping time corresponding to the optimized power factors (PFs) for each polymer, the doped P3POET film maintains both relatively high Seebeck coefficient (S) and electrical conductivity (σ) close to their maximum values, while the other polymers show either higher S and much lower σ (P3HT) or higher σ but much lower S (P3EOPT and P3MOBT). The square dependence of the PFs on S together with higher σ amplifies the power factor value of P3POET, which is almost 2 times those of the other polymers (11-13 μW m-1 K-2).
