Monophosphoramide derivatives: synthesis and crystal structure, theoretical and experimental studies of their biological effects.

Synthesizing new chemical compounds and studying their biological applications have been important issues in scientific research. In this investigation, we synthesized and characterized ten new N-acetyl phosphoramidate compounds and explored the crystal structure of three others. Furthermore, not only were some kinetic inhibition parameters measured, like IC50, Ki, kp, KD for 7 compounds on human acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), but also their hydrophobic parameter was determined by shake-flask technique. All compounds (number 1-10) were investigated for anti-bacterial activity against three Gram-positive and three Gram-negative bacteria, while chloramphenicol was used as a standard antibiotic. In order to find new insecticide, toxicities of 13 acephate (Ace)-derived compounds (number 20-32) were bioassayed on third larval instar of elm leaf beetle and Xanthogaleruca luteola. Additionally, screening in vivo tests revealed that two compounds had had the greatest insecticidal potential in comparison with others. It means these ones inhibited AChE (with mixed mechanisms) and general esterase more than the rest. According to ChE-QSAR models, the inhibitory potency for enzyme and bacteria is directly influenced by the electronic parameters versus structural descriptors. AChE-QSPR model of fluorescence assay indicated that the inhibitory power of AChE is primarily influenced by a set of electronic factors with the priority of: EHB > PL > δ(31P) versus structural descriptor (SA and Mv). Synthesizing new chemical compounds and studying their biological applications have been important issues in scientific research. Toxicities of 13 acephate (Ace)-derived compounds (number 20-32) were bioassayed on third larval instar of elm leaf beetle and Xanthogaleruca luteola. Insect-QSAR equations of these compounds, based on MLR and PCA, showed that non-descriptor net charge nitrogen atom (which was affected by the polarization of N-H group) had the greatest effect on insecticidal potential.

Tetra-kis(benzyl-amino)-phospho-nium chloride.

The title salt, [P(NHCH(2)C(6)H(5))(4)](+)·Cl(-), crystallizes with the P atom and Cl(-) anion lying on a twofold rotation axis. The P atom has a slightly distorted tetra-hedral geometry with two classes of N-P-N angles [101.15 (10) and 100.55 (11)° and 113.07 (9) and 114.83 (8)°] and the environments of sp(2)-hybridized N atoms are essentially planar (sum of angles = 359.9 and 360.1°). In the crystal, the phospho-nium ion inter-acts with each neighboring chloride ion via two approximately equal N-H⋯Cl inter-actions, forming parallel chains along the c axis.

Synthesis, characterization, oxidative degradation, antibacterial activity and acetylcholinesterase/butyrylcholinesterase inhibitory effects of some new phosphorus(V) hydrazides.

Some new phosphorus(V) hydrazides 1a-12a were synthesized and characterized by (1)H, (13)C, (31)P NMR, IR spectroscopy and elemental analysis. Moreover, the interaction of Cu(M)(2)·nH(2)O with 1a, 3a and 7a gave 4,4'-bis(morpholine)diazene (1b). In fact, in these reactions, copper(II) ions acted as oxidizing agent. The results supported the proposed mechanism. The structures of compounds 1a, 1b and 1c were further determined by X-ray crystallography. Compounds 1a-12a were screened for their antibacterial activities. Also, the acetyl- and butyrylcholinesterase inhibitory activity of 1a, 3a, 7a, 11a and 12a was measured using Ellman's method. It is interesting that these compounds were more potent inhibitors of BChE than of AChE. Also, using Lineweaver-Burk plots, it was indicated these compounds are mixed inhibitors.