151418-47-2

Basic information

• Product Name: N-(2-FORMYL-5,8-DIOXO-5,8-DIHYDROQUINOLIN-7-YL)ACETAMIDE
• Synonyms: N-(2-FORMYL-5,8-DIOXO-5,8-DIHYDROQUINOLIN-7-YL)ACETAMIDE
• CAS NO: 151418-47-2
• Molecular Formula: C₁₂H₈N₂O₄
• Molecular Weight: 244.2
• Mol File: 151418-47-2.mol

Chemical Properties

• Boiling Point: 563.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.45±0.1 g/cm3(Predicted)
• PKA: 10.24±0.20(Predicted)
• CAS DataBase Reference: N-(2-FORMYL-5,8-DIOXO-5,8-DIHYDROQUINOLIN-7-YL)ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-FORMYL-5,8-DIOXO-5,8-DIHYDROQUINOLIN-7-YL)ACETAMIDE(151418-47-2)
• EPA Substance Registry System: N-(2-FORMYL-5,8-DIOXO-5,8-DIHYDROQUINOLIN-7-YL)ACETAMIDE(151418-47-2)

Safety Data

• Hazardous Substances Data: 151418-47-2(Hazardous Substances Data)

Upstream product

• 162219-42-3 5,7-diacetamido-2-methyl-8-acetoxyquinoline 
• 826-81-3 2-methyl-8-quinolinol 
• 677761-30-7 5,7-diaamino-8-hydroxy-2-methylquinoline 
• 38543-75-8 8-hydroxy-2-methyl-5,7-dinitroquinoline 
• 151418-46-1 N-(2-methyl-5,8-dioxo-5,8-dihydroquinolin-7-yl)acetamide 
• 180208-49-5 N-(7-Acetylamino-8-hydroxy-2-methyl-quinolin-5-yl)-acetamide 

Downstream Products

• 1226517-44-7 7-N-acetyldemethyllavendmycin N-benzylpiperazine amide 
• 642478-73-7 7-N-acetyldemethyllavendamycin β-hydroxyethyl ester dibenzyl phosphate 

Relevant articles and documents

Total Synthesis of Novel 6-Substituted Lavendamycin Antitumor Agents

(Equation presented) Novel 6-substituted lavendamycins have been synthesized for the first time. The key step in these syntheses is a Pictet-Spengler condensation (Scheme 1). Efficient methods for the synthesis of each compound, including a novel reaction for the facile introduction of alkylamino groups at the C-6 position of the lavendamycin system, are discussed. Possible mechanisms for these reactions are also presented.

A highly concise synthesis of lavendamycin methyl ester

Lavendamycin methyl ester (2), an antitumor antibiotic, was synthesized by a practical and short route in an excellent overall yield of 33% from known starting materials. Pictet-Spengler condensation of 7-acetamido-2-formylquinoline-5,8-dione (4) with the methyl ester of (2RS,3SR)-β-methyltryptophan (5) followed by hydrolysis afforded 2. Aldehyde 4 was prepared by the oxidation of 7-acetamido-2-methylquinoline-5,8-dione (9). Dione 9 was obtained via the Diels-Alder condensation of the novel 1-[(tert-butyldimethylsilyl)oxy]-2-methyl-1-aza-1,3-butadiene (7) with 2-acetamido-6-bromobenzene-1,4-dione (8).

Lavendamycin analogues and methods of synthesizing and using lavendamycin analogues

Lavendamycin analogues, methods for their synthesis, and methods for their use in the treatment of diseases such as cancer and HIV infection are described.

Highly efficient and practical syntheses of lavendamycin methyl ester and related novel quinolindiones

The novel 7-(N-formyl-, 7-(N-acetyl-, and 7-(N-isobutyrylamino)-2-methylquinoline-5,8-diones were synthesized in excellent overall yields in three steps via the nitration of the commercially available 8-hydroxy-2-methylquinoline followed by a reduction-acylation step and then oxidation. Acid hydrolysis of 7-(N-acetylamino)-2-methylquinoline-5,8-dione (14a) afforded the novel 7-aminoquinoline-5,8-dione 7 in excellent yields. Due to our efficient preparation of dione 14a, we now report a short and practical method for the total synthesis of the potent antitumor agent lavendamycin methyl ester (1b) with an excellent overall yield.