5159-59-1Relevant articles and documents
Synthesis, crystal structure and dynamic behavior of naphthalene-based calix[3]amide: Cyclic trimers of 2-alkylamino-6-naphthoic acid
Katagiri, Kosuke,Sawano, Kanako,Okada, Miho,Yoshiyasu, Shiho,Shiroyama, Reiko,Ikejima, Norio,Masu, Hyuma,Kato, Takako,Tominaga, Masahide,Azumaya, Isao
, p. 346 - 350 (2008)
Treatment of 6-amino-2-naphthoic acid with dichlorotriphenylphosphorane afforded a new naphthalene ring-based calix[3]amide in moderate yield. The macrocyclic calix[3]amide exists in an anti-form in the crystalline state and forms a channel structure along its b axis. In CDCl3 solution it exists in equilibrium between the syn- and anti-forms in solution (100:57). The energy barrier between the anti- to syn-forms was calculated to be 17.8 ± 0.2 kcal/mol.
Nickel-Catalyzed Synthesis of Primary Aryl and Heteroaryl Amines via C-O Bond Cleavage
Yue, Huifeng,Guo, Lin,Liu, Xiangqian,Rueping, Magnus
supporting information, p. 1788 - 1791 (2017/04/11)
A nickel-catalyzed protocol for the conversion of aryl and heteroaryl alcohol derivatives to primary and secondary aromatic amines via C(sp2)-O bond cleavage is described. The new amination protocol can be applied to a range of substrates bearing diverse functional groups and uses readily available benzophenone imines as an effective nitrogen source.
Discovery of new photoactivatable diaryltetrazoles for photoclick chemistry via scaffold hopping
Yu, Zhipeng,Ho, Lok Yin,Wang, Zhiyong,Lin, Qing
supporting information; scheme or table, p. 5033 - 5036 (2011/10/09)
We report the discovery of two long-wavelength (365 nm) photoactivatable diaryltetrazoles through screening a small library of diaryltetrazoles that were designed using a 'scaffold hopping' strategy. A naphthalene-derived tetrazole showed excellent reacti
Synthesis of poly(naphthalenecarboxamide)s with low polydispersity by chain-growth condensation polymerization
Mikami, Koichiro,Daikuhara, Hiroaki,Kasama, Jyunya,Yokoyama, Akihiro,Yokozawa, Tsutomu
experimental part, p. 3020 - 3029 (2012/05/05)
Condensation polymerization of 6-(N-substituted-amino)-2-naphthoic acid esters (1) was investigated as an extension of chain-growth condensation polymerization (CGCP). Methyl 6-(3,7-dimethyloctylamino)-2-naphthoate (1b) was polymerized at -10 °C in the presence of phenyl 4-methylbenzoate (2) as an initiator and lithium 1,1,1,3,3,3-hexamethyldisilazide (LiHMDS) as a base. When the feed ratio [1a]0/[2]0 was 10 or 20, poly(naphthalenecarboxamide) with defined molecular weight and low polydispersity was obtained, together with a small amount of cyclic trimer. However, polymer was precipitated during polymerization under similar conditions in [1a]0/[2]0 = 34. To increase the solubility of the polymer, monomers 1c and 1d with a tri(ethylene glycol) (TEG) monomethyl ether side chain instead of the 3,7-dimethyloctyl side chain were synthesized. Polymerization of the methyl ester monomer 1c did not proceed well, affording only oligomer and unreacted 1c, whereas polymerization of the phenyl ester monomer 1d afforded well-defined poly(naphthalenecarboxamide) together with small amounts of cyclic oligomers in [1d]0/[2]0 = 10 and 29. The polymerization at high feed ratio ([1d]0/[2]0 = 32.6) was accompanied with self-condensation to give polyamide with a lower molecular weight than the calculated value. Such undesirable self-condensation would result from insufficient deactivation of the electrophilic ester moiety by the electron-donating resonance effect of the amide anion.
Modulation on C- and N-terminal moieties of a series of potent and selective linear tachykinin NK2 receptor antagonists
Gensini, Martina,Altamura, Maria,Dimoulas, Tula,Fedi, Valentina,Giannotti, Danilo,Giuliani, Sandro,Guidi, Antonio,Harmat, Nicholas J. S.,Meini, Stefania,Nannicini, Rossano,Pasqui, Franco,Tramontana, Manuela,Triolo, Antonio,Maggi, Carlo Alberto
scheme or table, p. 65 - 78 (2010/11/16)
Herein we describe the synthesis of a series of new potent tachykinin NK2 receptor antagonists by the modulation of the Cand N-terminal moieties of ibodutant (MEN 15596, 1). The Nterminal benzo[b]thiophene ring was replaced by different substituted naphthalenes and benzofurans, while further modifications were evaluated at the C-terminal tetrahydropyran moiety. Most compounds demonstrated a high affinity for the human NK2 receptor and high in vitro antagonist potency, indicating that a wide range of substituents at both termini can be incorporated in the molecule without detrimental effects on the interactions with the NK2 receptor. Selected compounds were tested in vivo confirming their activity as NK2 antagonists. In particular, after both iv and id administration to guinea pig, compound 61b was able to antagonize NK2-induced colonic contractions with a potency and duration-of-action fully comparable to the reference compound 1 (MEN 15596, ibodutant).
Trinaphthylamines as robust organic materials for two-photon-induced fluorescence
Bordeau, Guillaume,Lartia, Rémy,Metge, Germain,Fiorini-Debuisschert, Céline,Charra, Fabrice,Teulade-Fichou, Marie-Paule
supporting information; experimental part, p. 16836 - 16837 (2009/04/13)
The synthesis of a novel π-conjugated trinaphthylamines series is described. These original push?pull octupolar systems exhibit large two-photon action cross section (σφ up to 510 GM) increased by a factor of 2?3 as compared to their triphenylamines analogues. This substantial improvement of the two-photon absorption properties is attributed to the stronger donor character of the trinaphthyl core. Copyright
6-(4-Chlorophenyl)-3-substituted-thieno[3,2-d]pyrimidin-4(3H)-one-based melanin-concentrating hormone receptor 1 antagonist
Tavares, Francis X.,Al-Barazanji, Kamal A.,Bishop, Michael J.,Britt, Christy S.,Carlton, David L.,Cooper, Joel P.,Feldman, Paul L.,Garrido, Dulce M.,Goetz, Aaron S.,Grizzle, Mary K.,Hertzog, Donald L.,Ignar, Diane M.,Lang, Daniel G.,McIntyre, Maggie S.,Ott, Ronda J.,Peat, Andrew J.,Zhou, Hui-Qiang
, p. 7108 - 7118 (2011/05/18)
Genetic manipulation studies in mice at both the MCH receptor 1 (MCHR1) as well as the MCH peptide levels have implicated MCHR1 as a key player in energy homeostasis. The phenotype exhibited by these studies, that is, increased metabolic rate, resistance to high fat diet, and subsequent weight loss, has spurred considerable efforts to develop antagonists of MCHR1. In continuation of efforts directed toward this goal, the present work capitalizes on the putative binding mode of an MCH antagonist, resulting in the identification of several novel chemotypes that are potent and selective MCHR1 antagonists. In addition, the favorable pharmacokinetics of representative examples has allowed for the evaluation of an MCHR1 antagonist in a high fat diet-induced obese rodent model of obesity. The tolerability of the right-hand side of the template for diverse chemotypes accompanied by favorable effects on weight loss enhances the attractiveness of this template in the pursuit toward development of effective anti-obesity agents.
EP2 RECEPTOR AGONISTS
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Page/Page column 118, (2008/06/13)
A compound of Formula (I) or a salt, solvate and chemically protected form thereof, wherein: R5 is an optionally substituted C5-20 aryl or C4-20 alkyl group; A is selected from the group consisting of Formulae (Ai), (Aii), (Aiii) D is selected from Formulae (Di), (Dii), (Diii), (Div), (Dv) B is selected from the group consisting of Formulae (Bi), (Bii), (Biii), (Biv) (Bv).
