1,1,1-Trichloro-2,2-bis-(4-iodo-phen-yl)ethane.
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ABSTRACT:
SUBMITTER: Smith G
PROVIDER: S-EPMC3414957 | biostudies-literature |
REPOSITORIES: biostudies-literature
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Project description:In the structure of the title compound, C(22)H(27)Cl(3)O(2), which is the 4-but-oxy-phenyl analogue of the insecticidally active 4-meth-oxy-phenyl compound meth-oxy-chlor, the dihedral angle between the two benzene rings is 79.61 (11)°. Present also in the structure is an intra-molecular aromatic C-H⋯Cl inter-action.
| S-EPMC3414989 | biostudies-literature
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.
| S-EPMC3515304 | biostudies-other
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.
| S-EPMC4813487 | biostudies-literature
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:In the crystal structure of the title compound, C29H8F16I4O4, short I⋯I and I⋯F contacts, which can be understood as halogen bonds (XBs), represent the strongest inter-molecular inter-actions, consistent with the presence of I and F atoms, and the absence of H atoms, at the periphery of the mol-ecule. In addition, π-π stacking inter-actions between tetra-fluoro-iodo-phenyl (TFIP) groups and five short F⋯F inter-actions are present.
| S-EPMC3629626 | biostudies-literature
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.
| S-EPMC3435685 | biostudies-literature
Project description:In the title salt adduct, C(17)H(21)ClN(2) (2+)·2C(2)Cl(3)O(2) (-)·C(2)HCl(3)O(2), the Cl atom of the dication is disordered over two positions in a 0.915 (3):0.085 (3) ratio. The Cl atoms in the trichloroacetate anions and trichloroacetic acid molecule are also disordered, with refined site-occupation factors of 0.59 (3):0.41 (3), 0.503 (12):0.417 (12) and 0.653 (12):0.347 (12). The piperazine ring adopts a chair conformation, with puckering parameters Q(T) = 0.587 (3) Å, θ = 2.6 (2) and Φ 334 (6)°. In the crystal, neighbouring mol-ecules are linked by N-H⋯O, O-H⋯O, N-H⋯Cl, C-H⋯O and C-H⋯Cl hydrogen bonds, forming a three-dimensional network.
| S-EPMC3435716 | biostudies-literature
Project description:Crystals of the title compound, C(30)H(20)F(12)P(2) or R(2)PCH(2)CH(2)PR(2) (R = 4-C(6)H(4)CF(3)), were inadvertently prepared while attempting to recrystallize a crude sample of trans-Re(Cl)(N(2))(R(2)PCH(2)CH(2)PR(2))(2) from diethyl ether. The molecule lies on a center of inversion. One of the rings lies approximately in the P-C-C-P plane; the dihedral angle is 174.53°.The other ring is not quite perpendicular; the dihedral angle is 71.1°. The compound is isostructural with the R = Ph, 4-C(6)H(4)CH(3) and 4-C(6)H(4)CH(2)CH(3) analogues. It is well known that the basicity of phosphines and diphosphines can be altered by changing the electron-donating ability of R; however, the structural parameters for the title compound do not significantly differ from those of the aforementioned substituted-phenyl compounds.
| S-EPMC2960220 | biostudies-literature
Project description:The title compound, C(14)H(8)N(6)O(12), is centrosymmetric, the mid-point of the central C-C bond being located on an inversion centre. Two of the three independent nitro groups are disordered over two sites, with a site-occupancy ratio of 0.513 (3):0.487 (3). Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.
| S-EPMC3247438 | biostudies-literature
Project description:In the asymmetric unit of the crystal structure of the title compound, C(16)H(17)Cl(3)N(3)O(2)P, there are two crystallograph-ically independent mol-ecules, which form dimers via N-H?O hydrogen bonding between the N-H group and the P=O group. In the mol-ecular structure, the phosphoryl group is anti to the carbonyl group. The two benzene rings are oriented at dihedral angles of 54.3?(2) and 49.7?(2)° in the two independent mol-ecules.
| S-EPMC2971180 | biostudies-literature