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Literature summary extracted from

  • Yang, H.; Liu, T.; Qi, H.; Huang, Z.; Hao, Z.; Ying, J.; Yang, Q.; Qian, X.
    Design and synthesis of thiazolylhydrazone derivatives as inhibitors of chitinolytic N-acetyl-beta-D-hexosaminidase (2018), Bioorg. Med. Chem., 26, 5420-5426 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.2.1.52 (2Z)-2-[(2E)-[(naphthalen-1-yl)methylidene]hydrazinylidene]-3-(2-phenoxyethyl)-1,3-thiazolidin-4-one 56.4% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-2-(((E)-benzylidene)hydrazono)-3-((benzyloxy)methyl)thiazolidin-4-one 62.7% inhibition at 0.01 mM; 62.7% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-2-(((E)-benzylidene)hydrazono)-3-(2-phenoxyethyl)thiazolidin-4-one 79.4% inhibition at 0.01 mM Ostrinia furnacalis
3.2.1.52 (Z)-2-(((E)-naphthalen-1-ylmethylene)hydrazono)-3-(2-phenoxyethyl) thiazolidin-4-one 56.4% inhibition at 0.01 mM Ostrinia furnacalis
3.2.1.52 (Z)-2-(((E)-naphthalen-1-ylmethylene)hydrazono)-3-(2-phenoxyethyl)thiazolidin-4-one 35.5% inhibition at 0.01 mM Ostrinia furnacalis
3.2.1.52 (Z)-2-(((E)-naphthalen-1-ylmethylene)hydrazono)-3-(prop-2-yn-1-yl) thiazolidin-4-one 8.8% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-2-(((E)-naphthalen-1-ylmethylene)hydrazono)-3-(prop-2-yn-1-yl)thiazolidin-4-one 8.8% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-((2-chlorothiazol-5-yl)methyl)-2-(((E)-naphthalen-1-ylmethylene)hydrazono) thiazolidin-4-one 39% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-((2-chlorothiazol-5-yl)methyl)-2-(((E)-naphthalen-1-ylmethylene)hydrazono)thiazolidin-4-one 39% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-((3,5-dimethylisoxazol-4-yl)methyl)-2-(((E)-naphthalen-1-ylmethylene)hydrazono) thiazolidin-4-one 34.5% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-((3,5-dimethylisoxazol-4-yl)methyl)-2-(((E)-naphthalen-1-ylmethylene)hydrazono)thiazolidin-4-one 34.5% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-((benzyloxy)methyl)-2-(((E)-(4-bromo naphthalen-1-yl)methylene)hydrazono) thiazolidin-4-one 43.7% inhibition at 0.01 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-((benzyloxy)methyl)-2-(((E)-(4-bromonaphthalen-1-yl)methylene)hydrazono)thiazolidin-4-one 43.7% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-((benzyloxy)methyl)-2-(((E)-4-(dimethylamino)benzylidene)hydrazono)thiazolidin-4-one 63.5% inhibition at 0.01 mM; 63.5% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-((benzyloxy)methyl)-2-(((E)-naphthalen-1-ylmethylene)hydrazono) thiazolidin-4-one 85.9% inhibition at 0.1 mM, 35.5% inhibition at 0.01 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-((benzyloxy)methyl)-2-(((E)-naphthalen-1-ylmethylene)hydrazono)thiazolidin-4-one 85.9% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-((benzyloxy)methyl)-2-(((E)-naphthalen-2-ylmethylene)hydrazono)thiazolidin-4-one 59.8% inhibition at 0.01 mM; 59.8% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-(4-chlorobenzyl)-2-(((E)-naphthalen-1-yl methylene)hydrazono)thiazolidin-4-one 53.2% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-(4-fluorobenzyl)-2-(((E)-naphthalen-1-yl methylene)hydrazono)thiazolidin-4-one 41.7% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-(cyclobutylmethyl)-2-(((E)-naphthalen-1-ylmethylene)hydrazono)thiazolidin-4-one 9.0% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-(cyclopropylmethyl)-2-(((E)-naphthalen-1-ylmethylene)hydrazono)thiazolidin-4-one 1.0% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-allyl-2-(((E)-naphthalen-1-ylmethylene) hydrazono)thiazolidin-4-one 21.9% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 (Z)-3-ethyl-2-(((E)-naphthalen-1-ylmethylene) hydrazono)thiazolidin-4-one 28.1% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 6-(dimethylamino)-2-(2-([(5-methyl-1,3,4-thiadiazol-2-yl)methyl]amino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 95.9% inhibition at 0.1 mM Ostrinia furnacalis
3.2.1.52 additional information not inhibited by (Z)-3-methyl-2-(((E)-naphthalen-1-ylmethylene) hydrazono)thiazolidin-4-one Ostrinia furnacalis
3.2.1.52 NAG-thiazoline
-
 Ostrinia furnacalis
3.2.1.52 PUGNAc i.e. O-(2-acetamido-2-deoxy-D-glucopyranosylidenamino) N-phenylcarbamate Ostrinia furnacalis
3.2.1.52 TMG-chitobiomycin
-
 Ostrinia furnacalis
3.2.1.52 TMG-chitotriomycin
-
 Ostrinia furnacalis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.2.1.52 chitin + H2O Ostrinia furnacalis
-
 N-acetyl-beta-D-glucosamine
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.2.1.52 Ostrinia furnacalis
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.2.1.52 4-nitrophenyl N-acetyl-beta-D-glucosaminide + H2O
-
 Ostrinia furnacalis 4-nitrophenol + N-acetyl-beta-D-glucosamine
-
 ?
3.2.1.52 chitin + H2O
-
 Ostrinia furnacalis N-acetyl-beta-D-glucosamine
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.2.1.52 Hex1
-
 Ostrinia furnacalis
3.2.1.52 N-acetyl-beta-D-hexosaminidase
-
 Ostrinia furnacalis

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
3.2.1.52 0.0021
-
 (Z)-2-(((E)-benzylidene)hydrazono)-3-(2-phenoxyethyl)thiazolidin-4-one at pH 6.5 and 30°C Ostrinia furnacalis
3.2.1.52 0.0037
-
 (Z)-2-(((E)-benzylidene)hydrazono)-3-((benzyloxy)methyl)thiazolidin-4-one at pH 6.5 and 30°C Ostrinia furnacalis
3.2.1.52 0.0041
-
 (Z)-3-((benzyloxy)methyl)-2-(((E)-4-(dimethylamino)benzylidene)hydrazono)thiazolidin-4-one at pH 6.5 and 30°C Ostrinia furnacalis
3.2.1.52 0.0064
-
 (Z)-3-((benzyloxy)methyl)-2-(((E)-naphthalen-2-ylmethylene)hydrazono)thiazolidin-4-one at pH 6.5 and 30°C Ostrinia furnacalis
3.2.1.52 0.0071
-
 (Z)-2-(((E)-naphthalen-1-ylmethylene)hydrazono)-3-(2-phenoxyethyl) thiazolidin-4-one at pH 6.5 and 30°C Ostrinia furnacalis
3.2.1.52 0.0082
-
 (Z)-3-((benzyloxy)methyl)-2-(((E)-(4-bromo naphthalen-1-yl)methylene)hydrazono) thiazolidin-4-one at pH 6.5 and 30°C Ostrinia furnacalis
3.2.1.52 0.0102
-
 (Z)-3-((benzyloxy)methyl)-2-(((E)-naphthalen-1-ylmethylene)hydrazono) thiazolidin-4-one at pH 6.5 and 30°C Ostrinia furnacalis