Debromohymenialdisine

Base Information

• Chemical Name: Debromohymenialdisine
• CAS No.: 125118-55-0
• Molecular Formula: C₁₁H₁₁N₅O₂
• Molecular Weight: 245.241
• NSC Number: 607174
• DSSTox Substance ID: DTXSID00415332
• Nikkaji Number: J650.129J,J3.113.288F
• Wikidata: Q27459158
• ChEMBL ID: CHEMBL255465
• Mol file: 125118-55-0.mol

Synonyms:DBHA-SKF;debromohymenialdisine;debromohymenialdisine, (Z)-isomer;SK and F 108753;SK and F-108753;SKF 108753;SKF-108753

Chemical Property of Debromohymenialdisine

Chemical Property:

• PSA: 112.37000
• Density: 1.82g/cm³
• LogP: 0.09730
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 245.09127461
• Heavy Atom Count: 18
• Complexity: 482

Purity/Quality:

DBH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC(=O)C2=C(C1=C3C(=O)NC(=N3)N)C=CN2
• Isomeric SMILES: C\1CNC(=O)C2=C(/C1=C\3/C(=O)NC(=N3)N)C=CN2
• Uses: An antineoplastic agent, a protein kinase inhibitor isolated from Marine Organisms, Terrestrial Plants, and Microorganisms. A natural product

Technology Process of Debromohymenialdisine

There total 23 articles about Debromohymenialdisine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

4-(2-amino-5-oxo-4,5-dihydro-3H-imidazol-4-yl)-6,7-dihydro-1H-pyrrolo[2,3-c]azepin-8-one (872971-64-7) → (Z)-debromohymenialdisine (125118-55-0)

Guidance literature:

With ammonia; In water; at 100 ℃; microwave irradiation;

DOI:10.1021/ol052266m

Reference yield: 75.0%

4-[2-Amino-5-oxo-3,5-dihydro-imidazol-(4Z)-ylidene]-2,3-dibromo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one; hydrochloride → (Z)-debromohymenialdisine (125118-55-0)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In methanol; for 10h;

DOI:10.1021/jo991277o

Reference yield: 74.0%

4-(5-oxo-2-thioxo-imidazolidin-4-ylidene)-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one (649554-70-1) → (Z)-debromohymenialdisine (125118-55-0)

Guidance literature:

With tert.-butylhydroperoxide; ammonium hydroxide; In ethanol;

DOI:10.1016/j.tetlet.2003.10.074

upstream raw materials:

4-[2-Amino-5-oxo-3,5-dihydro-imidazol-(4Z)-ylidene]-1,7-bis-(2-trimethylsilanyl-ethoxymethyl)-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one

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

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

4-(5-oxo-2-thioxo-imidazolidin-4-ylidene)-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one

Downstream raw materials:

aldisin

guanidine nitrate

Refernces

• 1、 Portevin, Bernard,Golsteyn, Roy M.,Pierré, Alain,De Nanteuil, Guillaume. "An expeditious multigram preparation of the marine protein kinase inhibitor debromohymenialdisine". . p. 9263 - 9265. Retrieved 2003.
• 2、 Annoura, Hirokazu,Tatsuoka, Toshio. "Total Syntheses of Hymenialdisine and Debromohymenialdisine: Stereospecific Construction of the 2-Amino-4-Oxo-2-Imidazolin-5(Z)-Disubstituted Ylidene Ring System". . p. 413 - 416. Retrieved 1995.
• 3、 Papeo, Gianluca,Posteri, Helena,Borghi, Daniela,Varasi, Mario. "A new glycociamidine ring precursor: Syntheses of (Z)-hymenialdisine, (Z)-2-debromohymenialdisine, and (±)-endo-2-debromohymenialdisine". . p. 5641 - 5644. Retrieved 2007/10/03.