38489-93-9

Basic information

• Product Name: 2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone
• Synonyms: 2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone;5H-Indeno[5,6-d]-1,3-dioxole-5,6(7H)-dione 6-OxiMe;6-(HydroxyiMino)-6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-one
• CAS NO: 38489-93-9
• Molecular Formula: C₁₀H₇NO₄
• Molecular Weight: 205
• Product Categories: Amines;Aromatics;Heterocycles;Neurochemicals;Amines, Aromatics, Heterocycles, Neurochemicals
• Mol File: 38489-93-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility: DMSO
• CAS DataBase Reference: 2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone(38489-93-9)
• EPA Substance Registry System: 2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone(38489-93-9)

Safety Data

• Hazardous Substances Data: 38489-93-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone is used as a key intermediate in the preparation of nonneurotoxic tetralin and indan analogues, which have potential applications in the development of new drugs.
Used in Cancer Treatment:
2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone is used in the total synthesis of Papilistatin, a unique phenanthrene-1,10-dicarboxylic acid with good anticancer and antibacterial activity. Papilistatin has shown potential in treating various types of cancer and can be used as a therapeutic agent in cancer treatment.
Used in Antibacterial Applications:
2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone is also used in the synthesis of Papilistatin, which exhibits antibacterial properties. This makes it a valuable compound in the development of new antibiotics to combat bacterial infections.

Upstream product

• 2815-95-4 3-(1,3 benzodioxol-5-yl)propionic acid 
• 68996-81-6 3-benzo[1,3]dioxol-5-yl-propionyl chloride 
• 6412-87-9 5,6-methylenedioxy-1-indanone 
• 2373-80-0 3,4-(methylenedioxy)cinnamic acid 
• 120-57-0 piperonal 
• 110-46-3 isopentyl nitrite 

Downstream Products

• 1294495-52-5 (Z/E)-3-(2-bromo-6-methoxyphenyl)-2-(2-carboxy-4,5-methylenedioxyphenyl)acrylic acid methyl ester 
• 132741-81-2 6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine 

Relevant articles and documents

Formation of the 5-Benzonaphthopyran System during an Attempted Benzophenanthridine Synthesis

The condensation of the Schiff base 6 with the homophthalic anhydride 7 was used during elaboration of a compound, 9, suitable for closure of the B ring of the benzophenanthridine system.However, treatment of 9 with sodium hydride in THF resulted in formation of 3,4-dimethoxy-5-oxo-7-cyano-9,10-(methylenedioxy)-5-benzonaphthopyran (10) instead of the Dieckmann-Thorpe cyclization product 2.

First total synthesis of Papilistatin

Papilistatin has been isolated recently and found to have good anticancer and antibacterial activity. Papilistatin is a unique phenanthrene-1,10- dicarboxylic acid. The first total synthesis of papilistatin is described here with radical cyclisation as the key step.

Synthesis of 4-Aryl-2-benzazepine-1,5-diones by Photocyclization of N-(2-Arylethyl)phthalimides

The photocyclization of N-(2-arylethyl)phthalimides to 4-aryl-2-benzazepine-1,5-diones is described.We found that the presence of electron donating substituents on the aryl ring (as in 10a and b) is necessary for the cyclization process to occur.The procedure also allowed synthesis of 2-benzazepinediones with a carboxylate group at C3 (11c and d) which were obtained as 1:1 mixture of diastereoisomers.The results of irradiating phthalimides 12, which bear an oxygenated substituent at the benzylic position, depended on the nature of the substituent.Attempts to photocyclize N-(indan-2-yl)phthalimides 16 and the electron-rich phthalimide 23 failed.

Nonneurotoxic Tetralin and Indian Analogues of 3,4-(Methylenedioxy)amphetamine (MDA)

Four cyclic analgues of the psychoactive phenethylamine derivative 3,4-(methylenedioxy)amphetamine were studied.These congeners, 5,6- and 4,5-(methylenedioxy)-2-aminoindan (3a and 4a, respectively), and 6,7- and 5,6-(methylenedioxy)-2-aminotetralin (3b and 4b, respectively) were tested for stimulus generalization in the two-lever drug-discrimination paradigm.Two groups of rats were trained to discriminate either LSD tartrate (0.08 mg/kg) from saline, or (+/-)-MDMA*HCl (1.75 mg/kg) from saline.In addition, a 2-aminoindan (5a) and 2-aminotetralin (5b) congener of the hallucinogenic amphetamine 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) were also evaluated.None of the methylenedioxy compounds substituted in LSD-trained rats, while both 3a and 3b fully substituted in MDMA-trained rats.Compounds 4a and 4b did not substitute in MDMA-trained rats.Compounds 5a and 5b did not substitute in MDMA-trained rats, although 5a substituted in LSD-trained rats, but with relatively low potency compared to its open-chain counterpart.In view of the now well-established serotonin neurotoxicity of 3,4-(methylenedioxy)amphetamine and its N-methyl homologue 1, 3a and 3b were evaluated and compared to 1 for similar toxic effects following a single acute dose of 40 mg/kg sc.Sacrifice at 1 week showed that neither 3a nor 3b depressed rat cortical or hippocampal 5-HT or 5-HIAA levels nor were the number of binding sites (Bmax) depressed for paroxetine.By contrast, and in agreement with other reports, 1 significantly depressed all three indices of neurotoxicity.These results indicate that 3a and 3b have acute behavioral pharmacology similar to 1 but that they lack similar serotonin neurotoxicity.