Structure-Activity Relationships and Physiological Aspects of New Photosynthetic Electron Transport Inhibitors, 3-Alkylaminoalkyliden-2H-pyran-2,4(3H)-diones (APs)

1988 ◽  
Vol 43 (11-12) ◽  
pp. 857-861 ◽  
Author(s):  
Tadao Asami ◽  
Hiroyuki Koike ◽  
Yorinao Inoue ◽  
Nobutaka Takahashi ◽  
Shigeo Yoshida
Keyword(s):  
Electron Transport ◽  
Photosynthetic Electron Transport ◽  
Structural Requirement ◽  
Structure Activity Relationships ◽  
New Class ◽  
Structure Activity ◽  
Transport Inhibition ◽  
Transport Inhibitors

3-Aminoalkylidene-2H-pyran-2,4(3H)-diones (APs), possessing a conjugated enamino moiety which is common to cyanoacrylates and 2-aminoalkylidenecyclohexane-1,3-diones (ACs), were found as a new class of photosynthetic electron transport inhibitors. Although the structural requirement of APs for photosynthetic electron transport inhibition was very similar to that of cyanoacrylates and ACs, thermoluminescence measurements indicated that the binding manner of APs to D 1 protein was totally different from that of other inhibitors.

scholarly journals Synthesis and Antimycobacterial and Photosynthesis-Inhibiting Evaluation of 2-[(E)-2-Substituted-ethenyl]-1,3-benzoxazoles

2014 ◽  
Vol 2014 ◽  
pp. 1-11 ◽  
Author(s):  
Ales Imramovsky ◽  
Jan Kozic ◽  
Matus Pesko ◽  
Jirina Stolarikova ◽  
Jarmila Vinsova ◽  
...  
Keyword(s):  
Electron Transport ◽  
Photosystem Ii ◽  
Inhibitory Action ◽  
Spinacia Oleracea ◽  
Photosynthetic Electron Transport ◽  
Inhibiting Activity ◽  
Donor Side ◽  
Structure Activity Relationships ◽  
Structure Activity

A series of twelve 2-[(E)-2-substituted-ethenyl]-1,3-benzoxazoles was designed. All the synthesized compounds were tested against three mycobacterial strains. The compounds were also evaluated for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleraceaL.) chloroplasts. 2-[(E)-2-(4-Methoxyphenyl)ethenyl]-1,3-benzoxazole, 2-[(E)-2-(2,3-dihydro-1-benzofuran-5-yl)ethenyl]-1,3-benzoxazole and 2-{(E)-2-[4-(methylsulfanyl)phenyl]ethenyl}-1,3-benzoxazole showed the highest activity againstM. tuberculosis,M. kansasii,andM. avium, and they demonstrated significantly higher activity againstM. aviumandM. kansasiithan isoniazid. The PET-inhibiting activity of the most activeortho-substituted compound 2-[(E)-2-(2-methoxyphenyl)ethenyl]-1,3-benzoxazole was IC50= 76.3 μmol/L, while the PET-inhibiting activity ofpara-substituted compounds was significantly lower. The site of inhibitory action of tested compounds is situated on the donor side of photosystem II. The structure-activity relationships are discussed.

Photosystem II Inhibition by Pyran-enamine Derivatives

1993 ◽  
Vol 48 (3-4) ◽  
pp. 163-167
Author(s):  
Koichi Yoneyama ◽  
Yoshihiro Nakajima ◽  
Masaru Ogasawara ◽  
Hitoshi Kuramochi ◽  
Makoto Konnai ◽  
...  
Keyword(s):  
Electron Transport ◽  
Photosystem Ii ◽  
Thylakoid Membranes ◽  
Major Determinant ◽  
Ps Ii ◽  
Structure Activity Relationships ◽  
Structure Activity

Abstract Through the studies on structure-activity relationships of 5-acyl-3-(1-aminoalkylidene)-4-hydroxy-2 H-pyran-2,6(3 H)-dione derivatives in photosystem II (PS II) inhibition, overall lipophilicity of the molecule was found to be a major determinant for the activity. In the substituted N -benzyl derivatives, not only the lipophilicity but also the electronic and steric characters of the substituents greatly affected the activity. Their mode of PS II inhibition seemed to be similar to that of DCMU , whereas pyran-enamine derivatives needed to be highly lipophilic to block the electron transport in thylakoid membranes, which in turn diminished the permeability through biomembranes.

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