634151-15-8

Basic information

• Product Name: Ceratamine A
• Synonyms: 4-[(3,5-Dibromo-4-methoxyphenyl)methyl]-6-methyl-2-(methylamino)imidazo[4,5-d]azepin-5(6H)-one;Ceratamine A
• CAS NO: 634151-15-8
• Molecular Formula: C17H16Br2N4O2
• Molecular Weight: 468.14
• Product Categories: Bases & Related Reagents;Heterocycles;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 634151-15-8.mol

Chemical Properties

• Melting Point: 236 °C(Solv: methanol (67-56-1))
• Boiling Point: 543.271°C at 760 mmHg
• Flash Point: 282.36°C
• Appearance: /
• Density: 1.722g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.683
• PKA: 8.87±0.20(Predicted)
• CAS DataBase Reference: Ceratamine A(CAS DataBase Reference)
• NIST Chemistry Reference: Ceratamine A(634151-15-8)
• EPA Substance Registry System: Ceratamine A(634151-15-8)

Safety Data

• Hazardous Substances Data: 634151-15-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ceratamine A is used as a bioactive compound for its antimitotic properties. It has the potential to be developed into a pharmaceutical agent, particularly for targeting and disrupting the process of cell division in cancer cells, thereby inhibiting tumor growth and progression.
Used in Cancer Research:
In the field of cancer research, Ceratamine A is used as a tool to study the mechanisms of cell division and the development of cancer. Its antimitotic properties make it a valuable asset in understanding how cancer cells divide and proliferate, which can lead to the discovery of new therapeutic strategies and treatments for various types of cancer.
Used in Drug Development:
Ceratamine A is used as a lead compound in the development of new drugs targeting cancer. Its unique structure and activity can serve as a starting point for the design and synthesis of novel anticancer agents, potentially leading to more effective and targeted treatments for patients suffering from cancer.

InChI:InChI=1/C17H16Br2N4O2/c1-20-17-21-13-4-5-23(2)16(24)10(14(13)22-17)6-9-7-11(18)15(25-3)12(19)8-9/h4-5,7-8H,6H2,1-3H3,(H,20,22)

Upstream product

• 1509903-99-4 C₂₄H₂₄Br₃N₃O₃ 
• 1509903-98-3 C₂₄H₂₅Br₂N₃O₃ 
• 1509903-97-2 C₁₆H₁₉N₃O₂ 
• 1509903-95-0 C₁₅H₁₇N₃O₂ 
• 1509903-94-9 C₁₅H₁₆N₂O₂ 
• 1509903-92-7 C₁₆H₁₈N₂O₂ 
• 114114-00-0 1,3-dibromo-5-(iodomethyl)-2-methoxybenzene 
• 1509903-91-6 C₈H₁₀N₂O 
• 1509904-02-2 C₁₇H₂₀Br₂N₄O₂ 
• 1509904-01-1 C₂₅H₂₈Br₂N₄O₃ 
• 634151-16-9 ceratamine B 
• 74-88-4 methyl iodide 

Relevant articles and documents

Total synthesis of microtubule-stabilizing agent ceratamine A

The total synthesis of ceratamine A, a natural microtubule-stabilizing agent with unusual cellular effects, has been accomplished starting from 5-methoxybenzimidazole in 10 steps in an overall yield of 12.7%. The key steps in the synthesis involved the Schmidt rearrangement to construct the azepine ring, the alkylation of lactam to introduce the C-5 benzylic side chain, and the highly economical SNAr reaction to install the C-2 methylamine residue.

SYNTHETIC METHOD FOR CERATAMINE A AND B AND ANALOGS THEREOF

Methods are provided for preparing compounds of the general formula (I) wherein X1 is an aryl hydrocarbon group optionally substituted with one or more groups independently selected from —R, —NH2, —NHR, —NR2, —OH, —OR, —F, —Cl, —Br, —I, —CF3, —C(═O)OH, —C(═O)OR, —C(═O)NH2, —C(═O)NHR, and —C(═O)NR2; X2 is —H, —R, —NHR, —NR2, —OR, —F, —Cl, —Br, or —I; and R is C1 to C10 hydrocarbyl. The methods comprise a double-dehydrogenation reaction step in which a functionalized aminohydroazepinone skeleton comprising an aminoimidazole ring is reacted with 2-iodoxybenzene to form the imidazo[4,5-d]azepine ring system present in formula (I). Example methods comprising the double-dehydrogenation reaction step are provided as efficient synthetic routes to ceratamine A, ceratamine B, and the des-methyl analogs thereof.

A direct and efficient total synthesis of the tubulin-binding agents ceratamine A and B.; use of IBX for a remarkable heterocycle dehydrogenation

The total synthesis of the tubulin-binding agents ceratamine A and B is reported, along with des-methyl analogs, via a synthetic route that is high-yielding and operationally efficient. The synthetic route involved a Beckmann rearrangement to form an azep