85079-45-4

Basic information

• Product Name: (2Z,5Z)-5-[(6-bromo-1H-indol-3-yl)methylidene]-2-imino-1,3-dimethylimidazolidin-4-one
• CAS NO: 85079-45-4
• Molecular Formula: C₁₄H₁₃BrN₄O
• Molecular Weight: 333.1832
• Mol File: 85079-45-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 471.2°C at 760 mmHg
• Flash Point: 238.8°C
• Density: 1.63g/cm³
• Vapor Pressure: 4.74E-09mmHg at 25°C
• Refractive Index: 1.718
• CAS DataBase Reference: (2Z,5Z)-5-[(6-bromo-1H-indol-3-yl)methylidene]-2-imino-1,3-dimethylimidazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z,5Z)-5-[(6-bromo-1H-indol-3-yl)methylidene]-2-imino-1,3-dimethylimidazolidin-4-one(85079-45-4)
• EPA Substance Registry System: (2Z,5Z)-5-[(6-bromo-1H-indol-3-yl)methylidene]-2-imino-1,3-dimethylimidazolidin-4-one(85079-45-4)

Safety Data

• Hazardous Substances Data: 85079-45-4(Hazardous Substances Data)

Upstream product

• 34293-22-6 2-imino-1,3-dimethylimidazolidin-4-one 
• 17826-04-9 6-bromo-1H-indole-3-carbaldehyde 
• 56107-25-6 2-imino-1,3-dimethylimidazolidin-4-one hydroiodide 

Relevant articles and documents

In vitro structure-activity relationships of aplysinopsin analogs and their in vivo evaluation in the chick anxiety-depression model

Aplysinopsins are tryptophan-derived natural products that have been isolated from a variety of marine organisms and have been shown to possess a range of biological activities. In vitro receptor binding assays showed that of the 12 serotonin receptor subtypes, analogues showed a high affinity for the 5-HT2B and 5-HT2C receptor subtypes, with selectivity for 5-HT2B over 5-HT2C. While no conclusions could be drawn about the number and position of N-methylations, bromination at C-4 and C-5 of the indole ring resulted in greater binding affinities, with Ki's as low as 35 nM. This data, combined with previous knowledge of the CNS activity of aplysinopsin analogs, suggested that these compounds may have potential as leads for antidepressant drugs. Compounds 3c, 3u, and 3x were evaluated in the chick anxiety-depression model to assess their in vivo efficacy. Compound 3c showed a modest antidepressant effect at a dose of 30 nM/kg in the animal model.

Synthesis and characterization of aplysinopsin analogs

Three aplysinopsin analogs were synthesized by reacting 5-bromo-5-fluoro- and 6-bromoindole-3-carboxaldehyde with either creatinine or 2-imino-1,3-dimethyl-imidazolidin-4-one or 2-imino-1-methyl-3-ethylimidazolidin- 4-one Single crystal structures on 5-bromo-4′-de-N-methylaplysinopsin DMF solvate [from creatinine, space group P21/n, lattice parameters a = 13.117(3) A, b = 8.6663(15) A, c = 14.743(3) A, β = 99.538(10)° at 173 K], 5-fluoroaplysinopsin DMF solvate [from 2-imino1,3-dimethyl-imidazolidin-4-one, space group P21/c, lattice parameters a = 11.114(3) A, b = 19.118(2) A, c = 8.503(2) A, β = 112.290(7)°], and 6-bromoindole-3-carboxaldehyde (space group P21/n, lattice parameters a = 7.657(2) A, b = 7.933(2) A, c = 13.521(3) A, β = 99.046(13)°) have been determined. Characterizations include spectrometric identifications employing IR, UV, HRMS, and 1H and 13C NMR. 5-Bromo-4′-de-N- methylaplysinopsin and 5-fluoroapIysinopsin exist in the E configuration. Springer Science+Business Media, LLC 2008.