Naphtho[2,3-b]thiophene-3-carboxylic acid, 3-amino-2,3,4,9-tetrahydro-4,9-dioxo-, ethyl ester

Base Information

• Chemical Name: Naphtho[2,3-b]thiophene-3-carboxylic acid, 3-amino-2,3,4,9-tetrahydro-4,9-dioxo-, ethyl ester
• CAS No.: 368427-26-3
• Molecular Formula: C15H13NO4S
• Molecular Weight: 303.339
• Mol file: 368427-26-3.mol

Synonyms:

Chemical Property of Naphtho[2,3-b]thiophene-3-carboxylic acid, 3-amino-2,3,4,9-tetrahydro-4,9-dioxo-, ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Naphtho[2,3-b]thiophene-3-carboxylic acid, 3-amino-2,3,4,9-tetrahydro-4,9-dioxo-, ethyl ester

There total 8 articles about Naphtho[2,3-b]thiophene-3-carboxylic acid, 3-amino-2,3,4,9-tetrahydro-4,9-dioxo-, ethyl ester 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: 49.0%

(2RS,4R)-2-phenylthiazolidine-4-carboxylic acid ethyl ester (189228-43-1) + [1,4]naphthoquinone (130-15-4) → 3-amino-3-(ethoxycarbonyl)-2,3-dihydrothieno[2,3-b]naphtho-4,9-dione (368427-26-3) + 5,10-dioxo-1-phenyl-5,10-dihydro-benzo[g]isoquinoline-3-carboxylic acid ethyl ester

Guidance literature:

(2RS,4R)-2-phenylthiazolidine-4-carboxylic acid ethyl ester; [1,4]naphthoquinone; With 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; In acetonitrile; at 20 ℃; for 12h;

With hydrogenchloride; In chloroform; for 1h;

DOI:10.1016/S0040-4039(01)01035-8

Reference yield: 37.0%

[1,4]naphthoquinone (130-15-4) + (4R) ethyl 2-(4-methylphenyl)thiazolidine-4-carboxylate (368427-19-4) → 3-amino-3-(ethoxycarbonyl)-2,3-dihydrothieno[2,3-b]naphtho-4,9-dione (368427-26-3) + 5,10-dioxo-1-p-tolyl-5,10-dihydro-benzo[g]isoquinoline-3-carboxylic acid ethyl ester

Guidance literature:

[1,4]naphthoquinone; (4R) ethyl 2-(4-methylphenyl)thiazolidine-4-carboxylate; With 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; In acetonitrile; at 20 ℃; for 12h;

With hydrogenchloride; In chloroform; for 1h;

DOI:10.1016/S0040-4039(01)01035-8

Reference yield:

(4R)-ethyl-2-(4-chlorophenyl) thiazolidine-4-carboxylate (78979-47-2) + [1,4]naphthoquinone (130-15-4) → 3-amino-3-(ethoxycarbonyl)-2,3-dihydrothieno[2,3-b]naphtho-4,9-dione (368427-26-3) + 1-(4-chloro-phenyl)-5,10-dioxo-5,10-dihydro-benzo[g]isoquinoline-3-carboxylic acid ethyl ester

Guidance literature:

(4R)-ethyl-2-(4-chlorophenyl) thiazolidine-4-carboxylate; [1,4]naphthoquinone; With 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; In acetonitrile; at 20 ℃; for 12h;

With hydrogenchloride; In chloroform; water; for 1h;

DOI:10.1016/S0968-0896(03)00310-9

upstream raw materials:

(2RS,4R)-2-phenylthiazolidine-4-carboxylic acid ethyl ester

[1,4]naphthoquinone

(4R) ethyl 2-(4-methylphenyl)thiazolidine-4-carboxylate

(4R)-ethyl-2-(4-chlorophenyl) thiazolidine-4-carboxylate

Downstream raw materials:

3-[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino-3-ethoxycarbonyl-2,3-dihydrothiopheno[2,3-b]naphthalene-4,9-dione

3-[N-(tert-butoxycarbonyl)-L-phenylalanyl]amino-3-ethoxycarbonyl-2,3-dihydrothiopheno[2,3-b]naphthalene-4,9-dione

C₃₉H₃₂N₂O₇S

3-[(L-phenylalanyl)amino]naphtho[2,3-b]thiophene-4,9-dione trifluoroacetate

Refernces

Design, synthesis, and cytotoxic evaluation of a new series of 3-substituted spiro[(dihydropyrazine-2,5-dione)-6,3′-(2′,3′- dihydrothieno[2,3-b]naphtho-4′,9′-dione)] derivatives

10.1021/jm0612158

The study investigates the development of a new series of spirodiketopiperazine derivatives for their cytotoxic potential against various human tumor cell lines. The researchers synthesized these compounds by condensing the 3-amino-3(ethoxycarbonyl)-2,3-dihydrothieno[2,3-b]naphtho-4,9-dione system with various amino acids, followed by intramolecular lactamization. The study evaluated the cytotoxic activity of these derivatives against MCF-7 human breast carcinoma and SW 620 human colon carcinoma cell lines, revealing that certain isomers derived from Proline (Pro), Cysteine (Cys), and Methionine (Met) exhibited cytotoxic potency comparable to or greater than that of doxorubicin. The study also explored the topoisomerase II inhibition activity and DNA-binding properties of these compounds. The results suggest that these derivatives could potentially circumvent multiple-drug resistance mechanisms and have significant cytotoxic effects on various tumor cell lines, including those resistant to doxorubicin and cisplatin.