Synthesis and physiological activity of new organophosphorus pesticides of 1,3,2-oxazaphosphorinane series

Шипов, А. Г.; Genkina, G. K.; Аrtyushin, О. I.; Mndzhoyan, Z. O.; Gushchin, B. E.; Chumakova, E. I.; Roslavtseva, S. A.; Eremina, O. Yu.; Bakanova, E. I.; Kagan, Yu. S.; Ershova, E. A.; Mastryukova, T. A.; Кабачник, М. И.

doi:10.1007/bf00696722

Cited by 15 publications

(3 citation statements)

References 3 publications

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“…In consequence of their wide synthetic applicability and therapeutic importance (matrix metalloproteinase‐inhibitors,1 pesticidal2 and antimicrobial3 activities, and alkylating anti‐cancer drugs4), considerable interest has been focused on 1,3,2‐oxazaphosphinane 2‐oxides. However, the syntheses and mass spectrometric behavior of the corresponding 1,3,4,2‐oxadiazaphosphinane 2‐oxides have been studied less extensively.…”

Section: The 1342‐oxadiazaphosphinane‐2‐oxides Investigatedmentioning

confidence: 99%

Selective Gas Adsorption and Unique Structural Topology of a Highly Stable Guest‐Free Zeolite‐Type MOF Material with N‐rich Chiral Open Channels

Lǐ

et al. 2008

Chemistry A European J

365

131

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A new multifunctional di-topic tetrazolate-based ligand, 2,3-di-1H-tetrazol-5-ylpyrazine (H(2)dtp) has been designed and synthesized. The solvothermal reaction of this ligand with ZnCl(2) gave a robust guest-free three-dimensional zeolite-like chiral metal-organic framework (MOF) complex, [Zn(dtp)], which crystallized in chiral space group P6(1) and possessed chiral open channels with nitrogen-rich walls and the diameter of approximately 4.1 A. This framework presents a unique uniform etd (8,3) topology, is the first example of its type in MOFs, and exhibits high thermal stability with the decomposition temperature above 380 degrees C and permanent porosity. It is interesting that this material is able to selectively adsorb O(2) and CO(2) over N(2) gas, being a rare example in MOFs. In addition, C(2)H(2) and MeOH adsorption results show that although the framework channel holds nitrogen-rich walls that may provide H-bonding sites, no NH H-bond effect between the guest molecules and microporous surface was observed.

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Section: The 1342‐oxadiazaphosphinane‐2‐oxides Investigatedmentioning

confidence: 99%

Selective Gas Adsorption and Unique Structural Topology of a Highly Stable Guest‐Free Zeolite‐Type MOF Material with N‐rich Chiral Open Channels

Lǐ

et al. 2008

Chemistry A European J

365

131

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“…Furthermore, 1,3,2‐oxazaphosphorinan‐2‐thiones, especially those bearing p‐ nitrophenoxy and butylthio (XR = 4‐O 2 N‐C 6 H 4 , BuS) groups (Fig. ), exhibit high nematocide activity with low mammalian toxicity and have a strong synergistic effect on pyrethroid insecticides .…”

Section: Introductionmentioning

confidence: 99%

3,5‐Bis(arylidene)piperid‐4‐ones Containing 1,3,2‐Oxazaphosphorinane Moieties: Synthesis and Antitumor Activity

Шипов

Makarov

Petrovskii

et al. 2013

Heteroatom Chemistry

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Two novel series of phosphorus‐substituted 3,5‐bis(arylidene)piperid‐4‐ones bearing 1,3,2‐oxazaphosphorinane cycle either directly attached to the piperidone core through the PN bond (diamidophosphates 4) or connected with it via thiocarbamoyl linker (thioureas 5) were obtained by the phosphorylation of NH precursors with 2‐oxo‐1,3,2‐oxazaphosphorinane chloride or the reaction of the former ones with the corresponding cyclic isothiocyanate. According to the results of cytotoxicity screening against human carcinoma cell lines (A549, CaOv3, KB), thioureas 5 were more active than the diamidophosphates 4 bearing the same arylidene rings, with compounds with electron‐withdrawing side groups displaying IC50 in the micromolar range of 1.2–7 μM. © 2013 Wiley Periodicals, Inc. Heteroatom Chem 24:191–199, 2013; View this article online at http://wileyonlinelibrary.com. DOI 10.1002/hc.21082

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“…1 The 1,3,2-oxazaphosphinane ring system is found in alkylating anticancer drugs (cyclophosphamide and ifosfamide), numerous derivatives of which have been prepared to determine their structure-activity relationships. 2 Compounds containing a 1,3,2-oxazaphosphinane moiety were recently reported to possess matrix metalloproteinase-inhibitory, 3 pesticidal 4 and antimicrobial 5 activities. Phosphorus-stabilized carbanions derived from chiral 1,3,2-oxazaphosphinane 2-oxides have been widely used in the diastereoselective formation of carbon-carbon bonds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and steric structure of pyrrolidine- and piperidine-fused 1,3,4,2-oxadiazaphosphinanes

Martinek¹,

Szolnoki²,

Zalán³

et al. 2006

Arkivoc

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Pyrrolidine-and piperidine-fused 1,3,4,2-oxadiazaphosphinane 2-oxides were prepared by cyclization of the corresponding pyrrolidine-and piperidine-hydrazino alcohols by using phosphorus-containing reagents. Stereochemical and conformational analyses were carried out in order to determine the effect of the ring size on the conformational behavior of the nitrogenbridged bicyclic system. It was found that the chair conformation in the pyrrolidine-fused 1,3,4,2-oxadiazaphosphinane 2-oxides can be shifted toward twisted or distorted conformations.

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Synthesis and physiological activity of new organophosphorus pesticides of 1,3,2-oxazaphosphorinane series

Cited by 15 publications

References 3 publications

Selective Gas Adsorption and Unique Structural Topology of a Highly Stable Guest‐Free Zeolite‐Type MOF Material with N‐rich Chiral Open Channels

Selective Gas Adsorption and Unique Structural Topology of a Highly Stable Guest‐Free Zeolite‐Type MOF Material with N‐rich Chiral Open Channels

3,5‐Bis(arylidene)piperid‐4‐ones Containing 1,3,2‐Oxazaphosphorinane Moieties: Synthesis and Antitumor Activity

Synthesis and steric structure of pyrrolidine- and piperidine-fused 1,3,4,2-oxadiazaphosphinanes

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