2006
DOI: 10.1016/j.bmcl.2006.03.024
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A new non-azole inhibitor of ABA 8′-hydroxylase: Effect of the hydroxyl group substituted for geminal methyl groups in the six-membered ring

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Cited by 17 publications
(8 citation statements)
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“…39 (+)-AHI4 is a new inhibitor of ABA 8 -hydrolase, which has been synthesised with an a-axial hydroxyl group instead of the geminal methyls at C-6 characteristic of (+)-AHI1, (1 S,2 S)-(+)-6-nor-2 3 -dihydro-4 -deoxy-ABA. 40 Bicyclic analogues of abscisic acid have been shown to have enhanced biological activity in plants. 41 …”
Section: Monocyclofarnesanementioning
confidence: 99%
“…39 (+)-AHI4 is a new inhibitor of ABA 8 -hydrolase, which has been synthesised with an a-axial hydroxyl group instead of the geminal methyls at C-6 characteristic of (+)-AHI1, (1 S,2 S)-(+)-6-nor-2 3 -dihydro-4 -deoxy-ABA. 40 Bicyclic analogues of abscisic acid have been shown to have enhanced biological activity in plants. 41 …”
Section: Monocyclofarnesanementioning
confidence: 99%
“…(+)-AHI4 did not exhibit ABA activity, but the compound enhanced the effect of (+)-ABA upon simultaneous application of both to rice seedlings. The activity of 1 M ABA, at which the elongation inhibition ratio is 22%, was enhanced to 96% by addition of 30 M (+)-AHI4 [37]. This suggests that (+)-AHI4 inhibits 8'-hydroxylation of (+)-ABA in vivo.…”
Section: ) Ahi1mentioning
confidence: 93%
“…It follows, therefore, that an acidic hydrogen should be introduced directly on the ring carbon, instead of the methyl groups. Thus, we designed and synthesized AHI4, which has an axial hydroxy group instead of geminal methyl groups at C6' of AHI1 [37]. (+)-AHI4, which has the same configuration at C1' as (+)-ABA, strongly inhibited recombinant CYP707A3.…”
Section: ) Ahi1mentioning
confidence: 99%
“…Recently, crystal structures of the CRE1/AHK4 CHASE sensor domain (residues 126-395) in complex with natural and synthetic CKs have provided further be inhibitors of CYP707A3, which assists in the design of non-azole inhibitors [120] (Figure 4(A) and (B)). The unstable 8′-OH ABA is cyclized to form phaseic acid (PA, 71) and is subsequently reduced to dihydrophaseic acid (DPA, 72) and epi-DPA (Figure 4(A) and (B)).…”
Section: Abscisic Acidmentioning
confidence: 99%