38309-89-6Relevant academic research and scientific papers
A bis-urea naphthalene macrocycle displaying two crystal structures with parallel ureas
Geer, Michael F.,Smith, Mark D.,Shimizu, Linda S.
, p. 3665 - 3669 (2011)
Herein we synthesized a bis-urea macrocycle from 2,7-dimethylnaphthalene that displays an unusual parallel urea conformation. The naphthalenes also adopt a bowl shape over the anticipated parallel planar orientation. Crystallization of the macrocycle from different solvent systems affords two solvated forms. 1·DMSO·(H2O)2 has an extended columnar structure where parallel macrocycles are linked by intervening hydrogen bonded water molecules. In 1·(MeOH)2 direct hydrogen-bonds link the macrocycles into chains, which hydrogen-bond with methanol molecules to form a layered structure.
COMPOUNDS USEFUL IN HIV THERAPY
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Page/Page column 242, (2020/06/19)
The invention relates to compounds of Formula (I), (Ia), (Ib), (II) or (III), salts thereof, pharmaceutical compositions thereof, as well as therapeutic methods of treatment and prevention.
Design, synthesis and biological evaluation of low molecular weight CXCR4 ligands
Sakyiamah, Maxwell M.,Kobayakawa, Takuya,Fujino, Masayuki,Konno, Makoto,Narumi, Tetsuo,Tanaka, Tomohiro,Nomura, Wataru,Yamamoto, Naoki,Murakami, Tsutomu,Tamamura, Hirokazu
supporting information, p. 1130 - 1138 (2019/02/16)
The chemokine receptor CXCR4/stromal cell-derived factor-1 (SDF-1: CXCL12) signaling axis represents a crucial drug target due to its relevance to several diseases such as HIV-1 infection, cancer, leukemia, and rheumatoid arthritis. With the aim of enhancing the binding affinity and anti-HIV activity of a potent CXCR4 ligand as a lead, 23 low molecular weight compounds containing dipicolylamine (Dpa) and cyclam cationic moieties with varying spacers and spatial positioning were designed, synthesized and biologically evaluated. All of the synthesized compounds screened at 1.0 μM in the NanoBRET assay system exhibited >70% inhibition of the binding of a competitive probe TAMRA-Ac-TZ14011 (10 nM) to CXCR4 in the presence of zinc (II) ion. Furthermore, selected compounds 3, 8, 9, 19 and 21 with spatial distances between the next carbon to Dpa and the next carbon to cyclam within the range of 6.5–7.5 ? showed potent binding affinity selective for CXCR4 with IC50 values of 1.6, 7.9, 5.7, 3.5 and 4.5 nM, respectively, with corresponding high anti-HIV activity with EC50s of 28, 13, 21, 28 and 61 nM, respectively, in the presence of zinc (II) ion. Some compounds with remarkably more potent CXCR4-binding affinity than that of an initial lead were obtained. These compounds interact with different but overlapping amino acid residues of CXCR4. The present studies have developed new low molecular weight CXCR4 ligands with high CXCR4-binding and anti-HIV activities, which open avenue into the development of more potent CXCR4 ligands.
Distance between Metal Centres Affects Catalytic Efficiency of Dinuclear CoIII Complexes in the Hydrolysis of a Phosphate Diester
Bencze, Eva Szusanna,Zonta, Cristiano,Mancin, Fabrizio,Prins, Leonard J.,Scrimin, Paolo
, p. 5375 - 5381 (2018/10/26)
Dinuclear CoIII complex catalysed hydrolysis of bis-p-nitrophenylphosphate, a DNA model substrate, is reported. The catalysts were designed in such a way that the two CoIII ions cannot be contemporaneously involved in the complexation of the substrate or transition state. Experimental evidence of the involvement of such a remote metal centre in the catalysis of the hydrolysis of a phosphate diester is provided. This contribution amounts to a ca. 64-fold rate acceleration for the second-order rate constants of the best dinuclear complex over the mononuclear one, which is apparently due to general acid or H-bonding catalysis. Furthermore, there is significant distance dependence for this catalytic contribution and, in this case, it appears that the best distance (as estimated by DFT calculations) is ca. 7.7 ?. This may indicate that the presence of metal centres in close proximity, as required for mechanism proposals in which all metals are directly involved in transition-state coordination, is not the only option for rate acceleration in natural phosphate hydrolysis.
Helical Threads: Enantiomerically Pure Carbo[6]Helicene Oligomers
Schaack, Cédric,Sidler, Eric,Trapp, Nils,Diederich, Fran?ois
supporting information, p. 14153 - 14157 (2017/10/17)
We report the synthesis of enantiomerically pure carbo[6]helicene oligomers with buta-1,3-diyne-1,4-diyl bridges between the helicene nuclei. The synthesis of monomeric (±)-2,15-bis[(triisopropylsilyl)ethynyl]carbo[6]helicene was achieved in 25 % yield over six steps. Pure (+)-(P)- and (?)-(M)-enantiomers were obtained by HPLC on a chiral stationary phase. The dimeric (+)-(P)2- and (?)-(M)2-configured and the tetrameric (+)-(P)4- and (?)-(M)4-configured oligomers were obtained by sequential oxidative acetylenic coupling. The ECD spectra of the tetrameric oligomers displayed large Cotton effect intensities of Δ?=?851 m?1 cm?1 at λ=370 nm ((M)4-enantiomer). We transformed the buta-1,3-diyne-1,4-diyl bridge in the dimeric (P)2 and (M)2 oligomer by heteroaromatization into a thiene-2,5-diyl linker. Although the resulting chromophore showed reduced ECD intensities, it exhibited a remarkably strong fluorescence emission at 450–500 nm, with an absolute quantum yield of 25 %.
Synthesis and structures of dinuclear Silver(I) and Copper(II) complexes of a semirigid naphthalene-bridged bipyrazolyl ligand
Duan, Peng-Cheng,Jin, Rui-Wen,Wang, Zi-Xuan,Yang, Guang
, p. 448 - 454 (2013/09/02)
Reactions of a semirigid bipyrazole, 2,7-bis(4′-methylene-1H- 3′,5′-diphenylpyrazole) naphthalene (H2L) with Ag(I) or Cu(II) salts yielded four dinuclear complexes, namely, [Ag2(H 2L)2(NO3)2] (1), [Ag 2(H2L)2](ClO4)2 (2), [Ag2(H2L)2](BF4)2 (3), and [Cu2(H2L)2Cl4] (4). X-ray analysis illustrates that the three Ag(I) complexes are structurally similar and exhibit a rectangular shape, while the Cu(II) complex features an intramolecular π-stacking between two naphthalene-moieties and is much more compressed compared with those Ag(I) complexes. Two different conformations, namely cis, cis- and trans, trans-, have been observed for this bipyrazolyl ligand in its Ag(I) and Cu(II) complexes, respectively. Graphical Abstract: A semirigid naphthalene-bridged bipyrazole and its four dinuclear silver(I) or copper(II) complexes have been prepared and the crystal structures of the metal complexes have been studied by X-ray diffraction.[Figure not available: see fulltext.]
Trigonal prismatic Cu(i) and Ag(i) pyrazolato nanocage hosts: Encapsulation of S8 and hydrocarbon guests
Duan, Peng-Cheng,Wang, Zhao-Yang,Chen, Jing-Huo,Yang, Guang,Raptis, Raphael G.
supporting information, p. 14951 - 14954 (2013/10/22)
Two neutral hexanuclear trigonal prismatic cage molecules have been synthesized by coupling two planar triangular M3pz 3-panels, M = Cu(i) and Ag(i), in eclipsed geometry. The ～230 A3 cage volume can be either vacant or occupied by neutral guests. The crystal structures of the M6-cyclohexane and Ag 6-S8 host-guest species have been determined.
Secondary interactions in crystals of all ten isomers of Di(bromomethyl)naphthalene
Jones, Peter G.,Kus, Piotr
experimental part, p. 433 - 444 (2010/10/01)
The packing of all ten isomers of di(bromomethyl)naphthalene is analysed; nine of the structures were determined here, one (the 1,8-isomer) was already known. The 1,5- and 2,6-isomers display crystallographic inversion symmetry and the 2,7-isomer mirror symmetry through the central bond. For the 1,2-, 1,7- and 2,7-isomers, the bromomethyl groups point to the same side of the ring system, and for all other isomers to opposite sides. As expected, the molecules are linked into aggregates by various types of interactions: weak hydrogen bonds CH...Br, Br...Br interactions, CH...π contacts, π ...π stacking and Br...π contacts. The weak hydrogen bonds tend to be numerous but relativelyi; long, and do not combine to form readily recognisable patterns; a more readily assimilated view of the packing is based on the Br...Br interactions, which are observed for all isomers except 1,7 and 2,3, and in some cases lead to aggregation to form quadrilaterals or chains. With decreasing frequency, the interactions π ...π, C-H...π and Br...π are observed, but the latter are rare (just two examples) and very asymmetric, with contacts to only one or two carbons.
Synthesis of kurasoin B using phase-transfer-catalyzed acylimidazole alkylation
Christiansen, Michael A.,Butler, Aaron W.,Hill, Amanda R.,Andrus, Merritt B.
body text, p. 653 - 657 (2009/08/07)
The hydroxy ketone natural product kurasoin B is synthesized using a phase-transfer-catalyzed alkylation reaction with benzyloxyacetyl imidazole. A biscinchonidinium dimethylnaphthalene catalyst allowed for high yield and near complete selectivity (99% ee
