125118-55-0

Basic information

• Product Name: DBH
• Synonyms: 4-(2-AMINO-4-OXO-2-IMIDAZOLIN-5-YLIDENE)-4,5,6,7-TETRAHYDROPYRROLO[2,3-C] AZEPIN-8-ONE;DBH;(4Z)-4-(2-Amino-1,5-dihydro-5-oxo-4H-imidazol-4-ylidene)-4,5,6,7-tetrahydro-pyrrolo[2,3-c]azepin-8(1H)-one;(Z)-2-Debromohymenialdisine;(Z)-Debromohymenialdisine;SKF 108753;4-(2-Amino-1,5-dihydro-5-oxo-4H-imidazol-4-ylidene)-4,5,6,7-tetrahydro-pyrrolo[2,3-c]azepin-8(1H)-one;NSC 607174
• CAS NO: 125118-55-0
• Molecular Formula: C11H11N5O2
• Molecular Weight: 245.24
• Product Categories: Bases & Related Reagents;Heterocycles;Nucleotides;Protein Kinase Inhibitors and Activators
• Mol File: 125118-55-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.82g/cm³
• Refractive Index: 1.877
• CAS DataBase Reference: DBH(CAS DataBase Reference)
• NIST Chemistry Reference: DBH(125118-55-0)
• EPA Substance Registry System: DBH(125118-55-0)

Safety Data

• Hazardous Substances Data: 125118-55-0(Hazardous Substances Data)

Usage

Uses

An antineoplastic agent, a protein kinase inhibitor isolated from Marine Organisms, Terrestrial Plants, and Microorganisms. A natural product

InChI:InChI=1/C11H11N5O2/c12-11-15-8(10(18)16-11)6-2-4-14-9(17)7-5(6)1-3-13-7/h1,3,13H,2,4H2,(H,14,17)(H3,12,15,16,18)/b8-6+

Upstream product

• 634-97-9 pyrrole-2-carboxyl acid 
• 173286-03-8 Methanesulfonyloxy-[8-oxo-1,7-bis-(2-trimethylsilanyl-ethoxymethyl)-1,6,7,8-tetrahydro-pyrrolo[2,3-c]azepin-4-yl]-acetic acid ethyl ester 
• 173286-01-6 Hydroxy-[8-oxo-1,7-bis-(2-trimethylsilanyl-ethoxymethyl)-1,6,7,8-tetrahydro-pyrrolo[2,3-c]azepin-4-yl]-acetic acid ethyl ester 
• 161200-40-4 1,7-di(trimethylsilylethoxymethyl)-6,7-dihydropyrrolo[2,3-c]azepin-4,8(1H, 5H)dione 
• 161200-30-2 methyl 3-<(1H-pyrrole-2-carbonyl)amino>propionate 
• 5427-82-7 1H-pyrrole-2-carbonyl chloride 
• 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 
• 154569-13-8 (+/-)-hymenin 
• 72908-87-3 aldisin 
• 129053-83-4 3-[(1H-pyrrole-2-carbonyl)-amino]-propionic acid ethyl ester 
• 129053-84-5 3-<(1H-pyrrole-2-carbonyl)amino>propionic acid 
• 35302-72-8 pyrrol-2-yl trichloromethyl ketone 
• 872971-64-7 4-(2-amino-5-oxo-4,5-dihydro-3H-imidazol-4-yl)-6,7-dihydro-1H-pyrrolo[2,3-c]azepin-8-one 
• 649554-70-1 4-(5-oxo-2-thioxo-imidazolidin-4-ylidene)-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one 

Downstream Products

• 72908-87-3 aldisin 
• 113-00-8 guanidine nitrate 

Relevant articles and documents

Synthesis of C11N5 Marine Sponge Alkaloids: (±)-Hymenin, Stevensine, Hymenialdisine, and Debromohymenialdisine

The synthesis of C11N5 marine sponge alkaloids (±)-hymenin (1), stevensine (2), hymenialdisine (3), and debromohymenialdisine (4) is described. These natural products are the primary family members of the sponge metabolites that contain a fused pyrrolo[2,3-c]azepin-8-one ring system with either a 2-aminoimidazole (AI) or glycocyamidine appendage. The key steps in the synthesis centered around the generation of novel azafulvenium ions and their regioselective heterodimerization with AI in order to create the tricyclic core. A rarely used protodebromination/oxidation strategy was employed to selectively generate the desired α-bromo substitution pattern seen in hymenialdisine (3). In addition, the AI moiety was shown to be a useful precursor to the glycocyamidine unit found in 3 and 4, which suggests that AI-derived natural products may be the biogenic forerunners to glycocyamidine metabolites.

A Practical Synthesis of (Z)-Debromohymenialdisine

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WNT SIGNALING INHIBITORS, AND METHODS FOR MAKING AND USING THEM

The invention provides dBHD-based compositions and dBHD analog compositions, and pharmaceutical compositions comprising them, e.g., in the form of liposomes and nanoparticles comprising them, and methods of making and using them. In one embodiment, these dBHD analogs are used to inhibit a dysfunctional stem cell and/or a cancer (tumor) stem cell.