96134-80-4

Usage

InChI:InChI=1/C11H17N3O3S/c1-3-14(4-2)18(16,17)10-7-5-6-9(8-10)11(15)13-12/h5-8H,3-4,12H2,1-2H3,(H,13,15)

Upstream product

• 445298-39-5 C₁₂H₁₇NO₄S 
• 1576-46-1 <(Diethylamino)sulfonyl>benzoic Acid 
• 4025-64-3 3-Carboxybenzenesulfonyl chloride 

Downstream Products

• 96134-60-0 N,N-Diethyl-3-(5-phenyl-[1,3,4]oxadiazol-2-yl)-benzenesulfonamide 
• 96134-58-6 N,N-Diethyl-3-(5-methyl-[1,3,4]oxadiazol-2-yl)-benzenesulfonamide 
• 96134-57-5 N,N-Diethyl-3-[1,3,4]oxadiazol-2-yl-benzenesulfonamide 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel (E)-N′-(2,3-dihydro-1H-inden-1-ylidene) benzohydrazides as potent LSD1 inhibitors

Lysine specific demethylase 1 (LSD1) plays an important role in regulating histone lysine methylation at residues K4 and K9 on histone H3 and is recognized as an attractive therapeutic target in multiple malignancies. In this study, a series of novel (E)-N′-(2,3-dihydro-1H-inden-1-ylidene) benzohydrazides were synthesized and biologically evaluated for their potential LSD1 inhibitory effect. Among them, compounds 5a and 5n showed the most potent LSD1 inhibitory activity with IC50values of 1.4 and 1.7?nM, respectively, which were about 10 times more potent compared with (E)-N-(1-(5-chloro-2-hydroxyphenyl) ethylidene)-3-(morpholinosulf-only) benzohydrazide (J. Med. Chem. 2013, 56, 9496–9508; as reference compound). Compounds 5a and 5n also exhibited marked anti-proliferation activities against cancer cell lines that highly expressed LSD1. These results suggest that these optimized compounds might be served as promising LSD1 inhibitors against cancer, which merit further study.

Factors Which Influence the Formation of Oxadiazoles from Anthranilhydrazides and Other Benzoylhydrazines

The cyclization of o-aminobenzoylhydrazine (1a) and its 5-methyl derivative 1b with four equivalents and with one equivalent of triethyl orthoacetate (TEOA) was studied. 3-Amino-2-methyl-4(3H)-quinazolinone (2a), 3,4-dihydro-2-methyl-5H-1,3,4-benzotriazepin-5-one (3a) and an imino ether derivative of 2a, N-ethanimidic acid ethyl ester (4a) were obtained from the reaction of 1a with four equivalents of TEOA.These results were compared with those of Merour who isolated 2a and 3a using the same conditions.When 1a was treated with one equivalent of TEOA, 2a, 3a, and a new product, 2-(5-methyl-1,3,4-oxadiazol-2-yl)benzenamine (5a) were produced, and 4a was not.Similar results were obtained with the reactions of 1b with TEOA.Authentic samples of oxadiazoles 5a and b were prepared by alternate routes.Novel acid-catalyzed rearrangements of benzotriazepinones 3a and b, to mixtures of aminoquinazolinones 2a and b and oxadiazoles 5a and b, respectively, were found.The different relative amounts of aminoquinazolinones 2 and oxadiazoles 5 which were produced from these rearrangements allowed us to choose between two potential mechanism for these interesting rearrangements.Treatment of 5-nitrobenzoylhydrazine (37) with four equivalents of TEOA gave three products which were characterized, but did not lead to benzotriazepinone formation.