Synthesis and Insecticidal Activity of 3, 5-Dimethylbenzoyl Moiety Modified Analogues of &lt;i&gt;N&lt;/i&gt;-&lt;i&gt;tert&lt;/i&gt;-Butyl-&lt;i&gt;N&lt;/i&gt;′-(4-ethylbenzoyl)-3, 5-dimethylbenzohydrazide

善宏, 沢田; 春美, 中川; 芳久, 塚本; 利明, 矢内; 進二, 横井; 幹夫, 柳; 哲夫, 渡部

doi:10.1584/jpestics.27.365

Cited by 4 publications

(4 citation statements)

References 11 publications

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“…The alternate ring was constructed from 3,5-dimethyl benzoic acid 3. Rather than direct bromination of the acid [14], we found that esterification to the methyl ester followed by controlled bromination with N-bromosuccinimide and distillation provides pure and plentiful quantities of 3-bromomethyl-5-methyl benzoate. Subsequent de-esterification using HBr smoothly yields the corresponding carboxylic acid.…”

Section: Preparation and Purification Of Ligandsmentioning

confidence: 87%

“…A more comprehensive understanding of possible pleiotropic effects of ligand inducers and ⁄ or the switch components is essential for successful use of the EcR gene switch for in vivo applications such as gene therapy. The diacylhydrazine [13,14] nonsteroidal ecdysone agonists, such as Rheoswitch ligand 1 (RSL-1; Fig. 1), are reported to be an excellent inducer for EcR gene switches, supporting up to 9000-fold induction of reporter activity [15].…”

mentioning

confidence: 99%

“…Other steroidal ligands, such as ponasterone A (Pon A; Fig. 1), have also been reported as potential inducers of EcR-based gene switches [8,14]. In addition, other chemotypes, such as amidoketones (AMK) and tetrahydroquinolines (THQ), are also being developed as inducers of EcR gene switches [16][17][18][19][20] (Fig.…”

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confidence: 99%

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Effect of ecdysone receptor gene switch ligands on endogenous gene expression in 293 cells

Panguluri

Hormann

et al. 2007

The FEBS Journal

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Regulated gene expression may substantially enhance gene therapy. Correlated with structural differences between insect ecdysteroids and mammalian steroids, the ecdysteroids appear to have a benign pharmacology without adversely interfering with mammalian signaling systems. Consequently, the ecdysone receptor‐based gene switches are attractive for application in medicine. In the present study, the effect of inducers of ecdysone receptor switches on the expression of endogenous genes in HEK 293 cells was determined. Four ligand chemotypes, represented by a tetrahydroquinoline (RG‐120499), one amidoketone (RG‐121150), two ecdysteroids [20‐hydroxyecdysone (20E) and ponasterone A (Pon A)], and four diacylhydrazines (RG‐102240, RG‐102277, RG‐102398 and RG‐100864), were tested in HEK 293 cells. The cells were exposed to ligands at concentrations of 1 µm (RG‐120499) or 10 µm (all others) for 72 h and the total RNA was isolated and analyzed using microarrays. Microarray data showed that the tetrahydroquinoline ligand, RG‐120499 caused cell death at concentrations ≥ 10 µm. At 1 µm, this ligand caused changes in the expression of genes such as TNF, MAF, Rab and Reprimo. At 10 µm, the amidoketone, RG‐121150, induced changes in the expression of genes such as v‐jun, FBJ and EGR, but was otherwise noninterfering. Of the two steroids tested, 20E did not affect gene expression, but Pon A caused some changes in the expression of endogenous genes. At lower concentrations pharmacologically relevant for gene therapy, intrinsic gene expression effects of ecdysteroids and amidoketones may actually be insignificant. A fortiori, even at 10 µm, the four diacylhydrazine ligands did not cause significant changes in expression of endogenous genes in 293 cells and therefore should have minimum pleiotropic effects when used as ligands for the ecdysone receptor gene switch.

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Section: Preparation and Purification Of Ligandsmentioning

confidence: 87%

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confidence: 99%

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Effect of ecdysone receptor gene switch ligands on endogenous gene expression in 293 cells

Panguluri

Hormann

et al. 2007

The FEBS Journal

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“…Obtained by coupling 1 and 5b 9 (procedure B 1 ) to give a yellow viscous oil that was crystallized from dichloromethane/hexane (89% yield).…”

Section: Methodsmentioning

confidence: 99%

Aryl chain analogues of the biotin vitamers as potential herbicides. Part 3

Ashkenazi

Pinkert

Nudelman

et al. 2007

Pest Management Science

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Novel aryl chain isosters and analogues of 7-keto-8-aminopelargonic acid (KAPA) and 7,8-diaminopelargonic acid (DAPA), the vitamer intermediates involved in the biosynthetic pathway of biotin, possessing chain lengths of eight carbon atoms, were prepared and evaluated as potential herbicides. In the greenhouse test the most active compounds were the fluorinated derivative 9d and the selenophenyl/furan mixture 17m/17p, which were most active against Foxtail millet. In the more sensitive Arabidopsis test the most active substances were 9a and 17m, which displayed GR(50) (concentration of active compound causing 50% growth inhibition) values of 0.2 and 0.5 mg kg(-1) respectively (values of < 50 mg kg(-1) are considered herbicidal).

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Insect Hormone Receptors as a Target Molecule for Development of Insecticides Based on Genome Information

Masui¹

2004

J. Pestic. Sci.

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Synthesis and Insecticidal Activity of 3, 5-Dimethylbenzoyl Moiety Modified Analogues of <i>N</i>-<i>tert</i>-Butyl-<i>N</i>′-(4-ethylbenzoyl)-3, 5-dimethylbenzohydrazide

Abstract: Fourteen analogues were synthesized by rationally modifying the 3,5-dimethylbenzoyl moiety of RH-5992, and evaluated for insecticidal activity against the common cutworm (Spodoptera litura). Although several derivatives showed good insecticidal activity, they were less active than RH-5992.

Cited by 4 publications

References 11 publications

Effect of ecdysone receptor gene switch ligands on endogenous gene expression in 293 cells

Effect of ecdysone receptor gene switch ligands on endogenous gene expression in 293 cells

Aryl chain analogues of the biotin vitamers as potential herbicides. Part 3

Insect Hormone Receptors as a Target Molecule for Development of Insecticides Based on Genome Information

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