82005-12-7

Basic information

• Product Name: 10Z-HYMENIALDISINE
• Synonyms: HYMENIALDISINE;HD;4-(2-AMINO-4-OXO-2-IMIDAZOLIDIN-5-YLIDENE)-2-BROMO-4,5,6,7-TETRAHYDROPYRROLO[2,3-C]AZEPIN-8-ONE;10Z-HYMENIALDISINE;(4Z)-4-(2-Amino-1,5-dihydro-5-oxo-4H-imidazol-4-ylidene)-2-bromo-4,5,6,7-tetrahydro-pyrrolo[2,3-c]azepin-8(1H)-one;(Z)-Hymenialdisine;(Z)-4-(2-Amino-1,5-dihydro-5-oxo-4H-imidazol-4-ylidene)-2-bromo-4,5,6,7-tetrahydro-pyrrolo[2,3-c]azepin-8(1H)-one;Hymenialdesine
• CAS NO: 82005-12-7
• Molecular Formula: C11H10BrN5O2
• Molecular Weight: 324.13
• Product Categories: Protein Kinase Inhibitors and Activators;Heterocycles;Tyrosine Kinase Inhibitors
• Mol File: 82005-12-7.mol
• Article Data: 5

Chemical Properties

• Appearance: Light Yellow Solid
• Density: 2.2 g/cm³
• Refractive Index: 1.911
• Storage Temp.: -20°C
• CAS DataBase Reference: 10Z-HYMENIALDISINE(CAS DataBase Reference)
• NIST Chemistry Reference: 10Z-HYMENIALDISINE(82005-12-7)
• EPA Substance Registry System: 10Z-HYMENIALDISINE(82005-12-7)

Safety Data

• Hazardous Substances Data: 82005-12-7(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Solid

Uses

A potent inhibitor of a variety of kinases including MEK-1, GSK-3, and CKI. It also exhibits inhibition of the G2 cell cycle checkpoint at the micromolar concentrations. A marine sponge alkaloid, a natural product

InChI:InChI=1/C11H10BrN5O2/c12-6-3-5-4(7-10(19)17-11(13)16-7)1-2-14-9(18)8(5)15-6/h3,15H,1-2H2,(H,14,18)(H3,13,16,17,19)/b7-4+

Upstream product

• 161200-37-9 4-(2-amino-4-oxo-2-imidazolin-5-ylidene)-2-bromo-1,7-di(trimethyl-silylethoxymethyl)-4,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-one 
• 184887-86-3 4-(2-Amino-3H-imidazol-4-yl)-2,5-dibromo-6,7-dihydro-1H-pyrrolo[2,3-c]azepin-8-one 
• 321318-79-0 4-(2-Amino-5-oxo-4,5-dihydro-3H-imidazol-4-yl)-2,3-dibromo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one 
• 872971-59-0 3-[(5-bromo-1H-pyrrole-2-carbonyl)-amino]-propionic acid ethyl ester 
• 35302-72-8 pyrrol-2-yl trichloromethyl ketone 
• 129053-83-4 3-[(1H-pyrrole-2-carbonyl)-amino]-propionic acid ethyl ester 
• 96562-96-8 2-bromoaldisine 
• 872971-60-3 3-[(5-bromo-1H-pyrrole-2-carbonyl)-amino]-propionic acid 
• 50371-52-3 4,5-dibromopyrrol-2-yl trichloromethyl ketone 
• 154468-44-7 4,5-dibromo-1H-pyrrole-2-carboxylic acid (3-oxopropyl)amide 
• 154468-45-8 2,3-dibromo-6,7-dihydro-1H-pyrrolo<2,3-c>azepin-8-one 
• 154468-43-6 4,5-dibromo-N-<2-(1,3-dioxolan-2-yl)ethyl>pyrrole-2-carboxamide 
• 154569-13-8 (+/-)-hymenin 
• 184887-85-2 4-(2-Amino-5-bromo-3H-imidazol-4-yl)-2,3-dibromo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one 

Relevant articles and documents

A new glycociamidine ring precursor: Syntheses of (Z)-hymenialdisine, (Z)-2-debromohymenialdisine, and (±)-endo-2-debromohymenialdisine

(Chemical Equation Presented) The synthesis of the C11H 5 marine sponge alkaloids, (Z)-hymenialdisine and (Z)-2-debromohymenialdisine, is described. A key step was the condensation between aldisine or its monobromo derivative and a n

Synthetic method of hymenialdisine and its derivatives and their synthetic intermediates, and those synthetic intermediates

The present invention provides hymenialdisine or its derivatives having the formula (I): STR1 wherein X 1 is a halogen atom or a hydrogen atom and a process for production of the same. Further, synthetic intermediates are included in the invention. Hymenialdisine and its derivatives have inhibitory effects against protein kinase C and can be expected to have applications as a drug for the treatment of conditions where it is believed the activation of protein kinase C is involved.

Total Syntheses of Hymenialdisine and Debromohymenialdisine: Stereospecific Construction of the 2-Amino-4-Oxo-2-Imidazolin-5(Z)-Disubstituted Ylidene Ring System

The first total synthesis of hymenialdisine (1a) and debromohymenialdisine (1b) was achieved via a novel stereospecific construction of the 2-amino-4-oxo-2-imidazoline-5(Z)-disubstituted ylidine ring system.