Stereoselective response of tribolium castaneum herbst and Musca domestica L. against optically active 2-methoxy-5-phenyl-1,3,2-oxazaphospholidine 2-sulfide

Akinori Hirashima, Nagano Takeshi, Oishi Rou, Eto Morifusa

研究成果: ジャーナルへの寄稿記事

2 引用 (Scopus)

抄録

1. The optical isomers of 2-methoxy-5-phenyl-l,3,2-oxazaphospholidine 2-sulfide (5-PMOS) were synthesized by a chiral two-step phosphorylating method, and their absolute configurations and optical purities were determined by 1H-NMR. 2. (S)c(R)p-trans-5-PMOS showed the highest activity and the activity decreased in the order of (S)c(R)p-trans->(R)c(R)p-cis->(R)c(S)p-trans->(S)c(S)p-cis-5-PM OS in reducing larval growth and inhibiting acetylcholinesterase (AChE) of the red flour beetle Tribolium castaneum Herbst. 3. (R)c(R)p-cis-5-PMOS showed the highest anti-AChE activity followed by (R)c(S)p-trans- >(S)c(R)p-trans->(S)c(S)p-cis-5-PMOS, corresponding with insecticidal activity against Musca domestica L. 4. Optical isomers of 5-PMOS were not effective in stimulating adenylate cyclase prepared from ventral nerve cords of Periplaneta americana L. 5. The reversed stereospecificity between the T. castaneum larval growth-inhibitory and M. domestica insecticidal activities of 5-PMOS optical isomers is due to a stereospecific difference in the intrinsic potency of active form of 5-PMOS isomers as AChE inhibitors with the two insects.

元の言語英語
ページ(範囲)395-399
ページ数5
ジャーナルComparative Biochemistry and Physiology. Part C, Comparative
104
発行部数3
DOI
出版物ステータス出版済み - 1 1 1993

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Tribolium
Houseflies
Sulfides
Acetylcholinesterase
Periplaneta
Cholinesterase Inhibitors
Beetles
Flour
Growth
Adenylyl Cyclases
Insects
(1,3,2)oxazaphospholidine
Proton Magnetic Resonance Spectroscopy

All Science Journal Classification (ASJC) codes

  • Immunology
  • Pharmacology

これを引用

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title = "Stereoselective response of tribolium castaneum herbst and Musca domestica L. against optically active 2-methoxy-5-phenyl-1,3,2-oxazaphospholidine 2-sulfide",
abstract = "1. The optical isomers of 2-methoxy-5-phenyl-l,3,2-oxazaphospholidine 2-sulfide (5-PMOS) were synthesized by a chiral two-step phosphorylating method, and their absolute configurations and optical purities were determined by 1H-NMR. 2. (S)c(R)p-trans-5-PMOS showed the highest activity and the activity decreased in the order of (S)c(R)p-trans->(R)c(R)p-cis->(R)c(S)p-trans->(S)c(S)p-cis-5-PM OS in reducing larval growth and inhibiting acetylcholinesterase (AChE) of the red flour beetle Tribolium castaneum Herbst. 3. (R)c(R)p-cis-5-PMOS showed the highest anti-AChE activity followed by (R)c(S)p-trans- >(S)c(R)p-trans->(S)c(S)p-cis-5-PMOS, corresponding with insecticidal activity against Musca domestica L. 4. Optical isomers of 5-PMOS were not effective in stimulating adenylate cyclase prepared from ventral nerve cords of Periplaneta americana L. 5. The reversed stereospecificity between the T. castaneum larval growth-inhibitory and M. domestica insecticidal activities of 5-PMOS optical isomers is due to a stereospecific difference in the intrinsic potency of active form of 5-PMOS isomers as AChE inhibitors with the two insects.",
author = "Akinori Hirashima and Nagano Takeshi and Oishi Rou and Eto Morifusa",
year = "1993",
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T1 - Stereoselective response of tribolium castaneum herbst and Musca domestica L. against optically active 2-methoxy-5-phenyl-1,3,2-oxazaphospholidine 2-sulfide

AU - Hirashima, Akinori

AU - Takeshi, Nagano

AU - Rou, Oishi

AU - Morifusa, Eto

PY - 1993/1/1

Y1 - 1993/1/1

N2 - 1. The optical isomers of 2-methoxy-5-phenyl-l,3,2-oxazaphospholidine 2-sulfide (5-PMOS) were synthesized by a chiral two-step phosphorylating method, and their absolute configurations and optical purities were determined by 1H-NMR. 2. (S)c(R)p-trans-5-PMOS showed the highest activity and the activity decreased in the order of (S)c(R)p-trans->(R)c(R)p-cis->(R)c(S)p-trans->(S)c(S)p-cis-5-PM OS in reducing larval growth and inhibiting acetylcholinesterase (AChE) of the red flour beetle Tribolium castaneum Herbst. 3. (R)c(R)p-cis-5-PMOS showed the highest anti-AChE activity followed by (R)c(S)p-trans- >(S)c(R)p-trans->(S)c(S)p-cis-5-PMOS, corresponding with insecticidal activity against Musca domestica L. 4. Optical isomers of 5-PMOS were not effective in stimulating adenylate cyclase prepared from ventral nerve cords of Periplaneta americana L. 5. The reversed stereospecificity between the T. castaneum larval growth-inhibitory and M. domestica insecticidal activities of 5-PMOS optical isomers is due to a stereospecific difference in the intrinsic potency of active form of 5-PMOS isomers as AChE inhibitors with the two insects.

AB - 1. The optical isomers of 2-methoxy-5-phenyl-l,3,2-oxazaphospholidine 2-sulfide (5-PMOS) were synthesized by a chiral two-step phosphorylating method, and their absolute configurations and optical purities were determined by 1H-NMR. 2. (S)c(R)p-trans-5-PMOS showed the highest activity and the activity decreased in the order of (S)c(R)p-trans->(R)c(R)p-cis->(R)c(S)p-trans->(S)c(S)p-cis-5-PM OS in reducing larval growth and inhibiting acetylcholinesterase (AChE) of the red flour beetle Tribolium castaneum Herbst. 3. (R)c(R)p-cis-5-PMOS showed the highest anti-AChE activity followed by (R)c(S)p-trans- >(S)c(R)p-trans->(S)c(S)p-cis-5-PMOS, corresponding with insecticidal activity against Musca domestica L. 4. Optical isomers of 5-PMOS were not effective in stimulating adenylate cyclase prepared from ventral nerve cords of Periplaneta americana L. 5. The reversed stereospecificity between the T. castaneum larval growth-inhibitory and M. domestica insecticidal activities of 5-PMOS optical isomers is due to a stereospecific difference in the intrinsic potency of active form of 5-PMOS isomers as AChE inhibitors with the two insects.

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