2,2-Bis(4-but-oxy-phen-yl)-1,1,1-trichloro-ethane.
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ABSTRACT:
SUBMITTER: Smith G
PROVIDER: S-EPMC3414989 | biostudies-literature |
REPOSITORIES: biostudies-literature
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Project description:In the title compound, C(18)H(19)Cl(3)O(2), which is the 4-eth-oxy-phenyl analogue of the insecticidally active 4-meth-oxy-phenyl compound meth-oxy-chlor, the dihedral angle between the two benzene rings is 60.38?(13)°. An intra-molecular aromatic C-H?Cl inter-action is present.
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Project description:1,1,1-Trichloro-2,2-bis(p-chlorophenyl)ethane (DDT), the first organochlorine insecticide, and pyrethroid insecticides are sodium channel agonists. Although the use of DDT is banned in most of the world due to its detrimental impact on the ecosystem, indoor residual spraying of DDT is still recommended for malaria control in Africa. Development of resistance to DDT and pyrethroids is a serious global obstacle for managing disease vectors. Mapping DDT binding sites is necessary for understanding mechanisms of resistance and modulation of sodium channels by structurally different ligands. The pioneering model of the housefly sodium channel visualized the first receptor for pyrethroids, PyR1, in the II/III domain interface and suggested that DDT binds within PyR1. Previously, we proposed the second pyrethroid receptor, PyR2, at the I/II domain interface. However, whether DDT binds to both pyrethroid receptor sites remains unknown. Here, using computational docking of DDT into the Kv1.2-based mosquito sodium channel model, we predict that two DDT molecules can bind simultaneously within PyR1 and PyR2. The bulky trichloromethyl group of each DDT molecule fits snugly between four helices in the bent domain interface, whereas two p-chlorophenyl rings extend into two wings of the interface. Model-driven mutagenesis and electrophysiological analysis confirmed these propositions and revealed 10 previously unknown DDT-sensing residues within PyR1 and PyR2. Our study proposes a dual DDT-receptor model and provides a structural background for rational development of new insecticides.
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Project description:The title compound, C(32)H(24)N(6)O(2), has an inversion centre located at the mid-point of the central C-C bond of the diether bridging unit. The terminal pyridine rings are canted relative to the central pyridine ring, with dihedral angles of 12.98 (6) and 26.80 (6)°. The maximum deviation from the eight-atom mean plane, defined by the two bridging O and C atoms and the central pyridine ring, is 0.0383 (10)° for the N atom.
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Project description:BackgroundAlthough preconception 1,1,1-trichloro-2,2,bis(p-chlorophenyl)ethane (DDT) exposure and B-vitamin deficiencies have each been shown to negatively affect human reproductive outcomes, little is known about their joint effect.ObjectiveWe sought to examine whether B-vitamin sufficiency protects against adverse effects of DDT on clinical pregnancy (CP) and subclinical early pregnancy loss (EPL).DesignWe measured preconception concentrations of plasma B vitamins (vitamin B-6, vitamin B-12, and folate) and serum total DDT [sum of p,p' and o,p' isomers of DDT and 1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene] in 291 nulligravid women from Anhui, China, who were studied in 1996-1998. The women were followed prospectively from the time they stopped contraception until CP (gestational age ≥42 d) or 12 mo (whichever occurred first). EPL was identified by using daily urinary human chorionic gonadotropin. The women were categorized according to B-vitamin status (deficiency compared with sufficiency) and DDT concentration (high compared with low).ResultsOf 291 study women, a total of 385 conceptions (31% of which ended in EPL) and 265 CPs occurred. Compared with women with adequate B-vitamins and low DDT, incidence rates of CP were reduced in women with B-vitamin deficiency and a high DDT concentration (P < 0.05 for all). Most notably, in women with sufficient vitamin B-12, DDT was not associated with the incidence of CP; in contrast, in women with vitamin B-12 deficiency, high DDT was associated with a lower incidence of CP (HR: 0.44; 95% CI: 0.23, 0.84); and the test for interaction was significant (P < 0.05). The odds of EPL decreased by 45% (95% CI: 21%, 62%) for each interquartile distance increase in folate in women with high DDT concentrations, and the test for interaction was significant (P = 0.006).ConclusionsOur results provide suggestive evidence that vitamin B-12 and folate sufficiency may help protect against adverse reproductive effects of DDT exposure. Additional studies are needed to confirm our findings.
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Project description:The mol-ecule of the title compound, C(30)H(24)N(2)O(2)S(4), adopts a Z-shaped conformation. The terminal benzothia-zole ring systems are oriented at a dihedral angle of 60.81 (8)°, while the central benzene rings are twisted to each other by a dihedral angle of 13.56 (14)°. Weak inter-molecular C-H⋯π inter-actions are present in the crystal structure.
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Project description:In the title compound, C(27)H(16)F(6)N(2)O(6), the nitro groups are almost coplanar with the aromatic rings to which they are attached [dihedral angles = 3.5 (5) and 6.2 (3)°]. The dihedral angles between adjacent aromatic rings are 78.07 (8) and 71.11 (8)° for nitro-phen-yl/phenyl and 69.50 (8)° for phen-yl/phenyl. An inter-molecular C-H⋯π inter-action seems to be effective in the stabilization of the structure.
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Project description:The asymmetric unit of the title compound, C(20)H(14)Cl(3)NO, consists of two independent mol-ecules. In one mol-ecule, the chlorinated benzene ring forms dihedral angles of 12.00 (9) and 77.04 (9)° with the phenyl rings. The dihedral angle between the phenyl rings is 80.37 (10)°. The corresponding dihedral angles for the other mol-ecule are 26.34 (10), 62.98 (10) and 88.47 (11)°, respectively. One of the mol-ecules features an intra-molecular C-H⋯O hydrogen bond, which forms an S(6) ring motif. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into [100] chains. The chains are further linked by C-H⋯O and C-H⋯Cl hydrogen bonds into a three-dimensional network.
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Project description:The whole mol-ecule of the title compound, C16H18O4, is generated by twofold rotational symmetry; the twofold axis bis-ects the central C-C bond. The O-C-C-O torsion angle about the central C-C bond is 69.45 (16)°. Symmetry-related benzene rings are inclined to one another by 64.91 (8)°. In the crystal, mol-ecules are connected by C-H⋯O hydrogen bonds, forming a three-dimensional network.
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