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1.  Crystal structure of (E)-N-[(E)-3-(4-meth­oxy­phen­yl)allyl­idene]naphthalen-1-amine 
In the title compound, C20H17NO, the dihedral angle between the mean planes of the 4-meth­oxy­phenyl ring and the naphthalene ring is 69.50 (7)°. The meth­oxy group is almost coplanar with the benzene ring to which it is connected [Cb—Cb—Om—Cm torsion angle of −7.9 (2)°; b = benzene and m = meth­oxy] and the imine group displays a C—C—N=C torsion angle is −57.2 (2)°. The imine (C=N) group has an E conformation. In the crystal, weak π–π inter­actions between the benzene rings [centroid–centroid distance = 3.7781 (10) Å] are observed.
doi:10.1107/S1600536814022521
PMCID: PMC4257298  PMID: 25484813
crystal structure; naphthalene derivative; π–π inter­actions
2.  9-[(E)-2-(4-Chloro­phen­yl)ethen­yl]-3,3,6,6-tetra­methyl-2,3,4,5,6,7,8,9-octa­hydro-1H-xanthene-1,8-dione 
In the title compound, C25H27ClO3, each of the cyclo­hexenone rings adopts an envelope conformation, whereas the six-membered pyran ring adopts a flattened boat conformation, with the O and methine C atoms deviating from the plane of the other four atoms. The C=C double bond is in the trans conformation. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into chains running parallel to the b axis.
doi:10.1107/S1600536813025026
PMCID: PMC3790409  PMID: 24098228
3.  (E)-2,2′-[3-(4-Chloro­phen­yl)prop-2-ene-1,1-di­yl]bis­(3-hy­droxy-5,5-di­methyl­cyclo­hex-2-en-1-one) 
The title compound, C25H29ClO4, adopts a trans conformation about the C=C double bond and the di­methyl­cyclo­hexenone rings both show an envelope conformation with the dimethyl-substituted C atom as the flap. In the mol­ecule, the hy­droxy and carbonyl groups form two intra­molecular O—H⋯O hydrogen bonds typical for xanthene derivatives. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into chains running parallel to the a-axis direction.
doi:10.1107/S1600536813020357
PMCID: PMC3793826  PMID: 24109413
4.  (E)-N-(3,3-Di­phenyl­allyl­idene)naph­thal­en-1-amine 
The title compound, C25H19N, adopts an E conformation about the C=N bond. The naphthalene ring system and the phenyl rings form dihedral angles 38.1 (1), 46.9 (8) and 48.5 (1)°, respectively, with the mean plane of the central enimino fragment. The crystal packing exhibits no directional close contacts.
doi:10.1107/S1600536813014888
PMCID: PMC3772462  PMID: 24046605
5.  (E)-9-(4-Fluoro­styr­yl)-3,3,6,6-tetra­methyl-3,4,5,6,7,9-hexa­hydro-2H-xanthene-1,8-dione 
In the title compound, C25H27FO3, each of the cyclo­hexenone rings adopts a half-chair conformation, whereas the six-membered pyran ring adopts a flattened boat conformation, with the O and methine C atoms deviating by 0.0769 (15) and 0.196 (2) Å, respectively, from the plane of the other four atoms (r.m.s. deviation = 0.004 Å). The C=C double bond adopts an E conformation. The dihedral angle between the benzene and pyran (all atoms) rings is 89.94 (10)°. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into chains running parallel to the b axis.
doi:10.1107/S1600536813014049
PMCID: PMC3685118  PMID: 23795137
6.  (E)-N-(3,3-Di­phenyl­allyl­idene)-2-(tri­fluoro­meth­yl)aniline 
In the title compound, C22H16F3N, the C=N bond of the central imine group adopts an E conformation. The dihedral angles between the 2-(tri­fluoro­meth­yl)phenyl ring and the benzene rings are 9.34 (1) and 68.8 (1)°. The imine group displays a C—C—N=C torsion angle of 41.6 (3)°. In the crystal, weak C—H⋯F hydrogen bonds link the mol­ecules into chains parallel to the b-axis direction.
doi:10.1107/S1600536813010283
PMCID: PMC3648283  PMID: 23723903
7.  (E)-N-[(E)-3-(4-Nitro­phen­yl)allyl­idene]naphthalen-1-amine 
In the title compound, C19H14N2O2, the dihedral angle between the mean planes of the 4-nitro­phenyl ring and the naphthalene ring system is 12.79 (2)°. The imine group displays a C—C—N=C torsion angle of 41.0 (2)° and the C=N group has an E conformation. In the crystal, weak C—H⋯O hydrogen bonds link molecules into layers parallel to the b axis.
doi:10.1107/S1600536813006417
PMCID: PMC3629600  PMID: 23634087
8.  (E)-2,2′-[3-(4-Fluoro­phen­yl)prop-2-ene-1,1-di­yl]bis­(3-hy­droxy-5,5-dimethyl­cyclo­hex-2-en-1-one) 
In the title compound, C25H29FO4, each cyclo­hexenone ring has an envelope conformation with the dimethyl-substituted atom as the flap. The hy­droxy and carbonyl groups form two intra­molecular O—H⋯O hydrogen bonds, as is typical for xanthene derivatives. In the crystal, very weak C—H⋯O hydrogen bonds link mol­ecules into dimers.
doi:10.1107/S1600536813004364
PMCID: PMC3588420  PMID: 23476580
9.  (E)-N-(3,3-Diphenyl­allyl­idene)-3-nitro­aniline 
In the title compound, C21H16N2O2, the 3-nitro­phenyl and two phenyl rings are twisted from the mean plane of the enimino fragment by 44.4 (1), 37.2 (1) and 74.1 (1)°, respectively. The crystal packing exhibits no classical inter­molecular contacts.
doi:10.1107/S1600536812040354
PMCID: PMC3470384  PMID: 23125797
10.  (E)-N-(3,3-Diphenyl­allyl­idene)-4-nitro­aniline 
In the title compound, C21H16N2O2, the dihedral angles between the mean planes of the 4-nitro­phenyl ring and the two phenyl rings are 57.3 (5) and 16.8 (6)°. The imine group displays a C—C—N—C torsion angle of −24.9 (3)°.
doi:10.1107/S1600536812040391
PMCID: PMC3470385  PMID: 23125798
11.  2,2′-[(E)-3-(4-Nitro­phen­yl)prop-2-ene-1,1-di­yl]bis­(3-hy­droxy-5,5-dimethyl­cyclo­hex-2-en-1-one) 
In the title compound, C25H29NO6, each of the cyclo­hexenone rings adopts a half-chair conformation. The hy­droxy and carbonyl O atoms face each other and are oriented to allow for the formation of two intra­molecular O—H⋯O hydrogen bonds. In the crystal, weak C—H⋯O hydrogen bonds are formed between molecules, generating a two-dimensional supramolecular structure.
doi:10.1107/S1600536812032242
PMCID: PMC3414961  PMID: 22904948
12.  (E)-3,3,6,6-Tetra­methyl-9-(2-nitro­styr­yl)-3,4,5,6,7,9-hexa­hydro-1H-xanthene-1,8(2H)-dione 
In the title compound, C25H27NO5, each of the cyclo­hexenone rings adopts a half-chair conformation, whereas the six-membered pyran ring adopts a flattened boat conformation, with the O and methine C atoms deviating from the plane of the other four atoms. In the crystal, weak C—H⋯O hydrogen bonds link mol­ecules into chains parallel to the c axis.
doi:10.1107/S1600536812023495
PMCID: PMC3379499  PMID: 22719697
13.  (E)-9-(4-Chloro­styr­yl)-3,4,5,6,7,9-hexa­hydro-2H-xanthene-1,8-dione 
In the title compound, C21H19ClO3, the two cyclo­hexenone rings adopt half-chair conformations, whereas the pyran ring adopts a boat conformation. The 4-chloro­phenyl ring is almost perpendicular to the plane through the four C atoms of the pyran ring [dihedral angle = 87.97 (6)°]. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into a chain parallel to the a-axis.
doi:10.1107/S1600536812002139
PMCID: PMC3275246  PMID: 22347102
14.  9-[(E)-2-(2-Meth­oxy­phen­yl)ethen­yl]-3,4,5,6,7,9-hexa­hydro-2H-xanthene-1,8-dione 
In the title compound, C22H22O4, the two cyclo­hexenone rings adopt half-chair conformations, whereas the six-membered pyran ring adopts a flattened boat conformation, with the O and methine C atoms deviating from the plane of the other four atoms by 0.142 (2) and 0.287 (2)Å, respectively. In the crystal, weak C—H⋯O hydrogen bonds link mol­ecules into chains running parallel to the a axis.
doi:10.1107/S1600536812001419
PMCID: PMC3275209  PMID: 22347065
15.  (E)-2,2′-[3-(2-Nitro­phen­yl)prop-2-ene-1,1-di­yl]bis­(3-hy­droxy­cyclo­hex-2-en-1-one) 
In the title compound, C21H21NO6, each of the cyclo­hexenone rings adopts a half-chair conformation. Each of the pairs of hy­droxy and carbonyl O atoms are oriented to allow for the formation of intra­molecular O—H⋯O hydrogen bonds, which are typical of xanthene derivatives.
doi:10.1107/S1600536811054730
PMCID: PMC3254576  PMID: 22259527
16.  [2-(4-Chloro­phen­yl)-5-phenyl­oxolan-3-yl](cyclo­penten­yl)methanone 
In the title compound, C22H21ClO2, the oxolane ring adopts a twisted conformation. The dihedral angles between the mean plane of the oxolane ring and the mean planes of the 4-chloro­phenyl, phenyl and cyclo­pentenyl rings are 71.81 (18), 76.9 (18) and 82.08 (18)°, respectively.
doi:10.1107/S1600536811051993
PMCID: PMC3254405  PMID: 22259548
17.  2,2-[(E)-3,3-Diphenyl­prop-2-ene-1,1-di­yl]bis­(3-hy­droxy­cyclo­hex-2-en-1-one) 
In the title compound, C27H26O4, each of the cyclo­hexenone rings adopts a half-chair conformation. The dihedral angle between the two phenyl rings is 89.53 (5)°. The hy­droxy and carbonyl O atoms face each other and are orientated to allow the formation of two intra­molecular O—H⋯O hydrogen bonds, which are typical of xanthene derivatives.
doi:10.1107/S1600536811048355
PMCID: PMC3239045  PMID: 22199893
18.  (E)-2,2′-[3-(2-Nitro­phen­yl)prop-2-ene-1,1-di­yl]bis­(3-hy­droxy-5,5-dimethyl­cyclo­hex-2-en-1-one) 
In the title compound, C25H29NO6, each of the cyclo­hexenone rings adopts a half-chair conformation. Each of the pairs of hy­droxy and carbonyl O atoms are oriented to allow for the formation of intra­molecular O—H⋯O hydrogen bonds, which are typical of xanthene derivatives. The nitro group is rotationally disordered over two orientations in a 0.544 (6):0.456 (6) ratio. In the crystal, weak inter­molecualr C—H⋯O hydrogen bonds link mol­ecules into layers parallel to the ab plane.
doi:10.1107/S1600536811043686
PMCID: PMC3238826  PMID: 22199679
19.  3-Hy­droxy-2-[(2E)-1-(2-hy­droxy-6-oxocyclo­hex-1-en-1-yl)-3-(2-meth­oxy­phen­yl)prop-2-en-1-yl]cyclo­hex-2-en-1-one 
In the title compound, C22H24O5, each of the cyclo­hexenone rings adopts a half-chair conformation. The hy­droxy and carbonyl O atoms face each other and are orientated to allow for the formation of the two intra­molecular O—H⋯O hydrogen bonds which are typical of xanthene derivatives. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link mol­ecules into layers parallel to the ab plane.
doi:10.1107/S1600536811038207
PMCID: PMC3201272  PMID: 22065620
20.  Development of selective blockers for Ca2+-activated Cl- channel using Xenopus laevis oocytes with an improved drug screening strategy 
Molecular Brain  2008;1:14.
Background
Ca2+-activated Cl- channels (CaCCs) participate in many important physiological processes. However, the lack of effective and selective blockers has hindered the study of these channels, mostly due to the lack of good assay system. Here, we have developed a reliable drug screening method for better blockers of CaCCs, using the endogeneous CaCCs in Xenopus laevis oocytes and two-electrode voltage-clamp (TEVC) technique.
Results
Oocytes were prepared with a treatment of Ca2+ ionophore, which was followed by a treatment of thapsigargin which depletes Ca2+ stores to eliminate any contribution of Ca2+ release. TEVC was performed with micropipette containing chelerythrine to prevent PKC dependent run-up or run-down. Under these conditions, Ca2+-activated Cl- currents induced by bath application of Ca2+ to oocytes showed stable peak amplitude when repetitively activated, allowing us to test several concentrations of a test compound from one oocyte. Inhibitory activities of commercially available blockers and synthesized anthranilic acid derivatives were tested using this method. As a result, newly synthesized N-(4-trifluoromethylphenyl)anthranilic acid with trifluoromethyl group (-CF3) at para position on the benzene ring showed the lowest IC50.
Conclusion
Our results provide an optimal drug screening strategy suitable for high throughput screening, and propose N-(4-trifluoromethylphenyl)anthranilic acid as an improved CaCC blocker.
doi:10.1186/1756-6606-1-14
PMCID: PMC2585076  PMID: 18959787

Results 1-20 (20)