Virstatin

Base Information

• Chemical Name: Virstatin
• CAS No.: 88909-96-0
• Molecular Formula: C₁₆H₁₃NO₄
• Molecular Weight: 283.284
• Hs Code.: 2933990090
• European Community (EC) Number: 694-826-4
• UNII: 24SR2Q1Y6M
• DSSTox Substance ID: DTXSID10237406
• Nikkaji Number: J2.252.165I
• Wikipedia: Virstatin
• Wikidata: Q24976752
• ChEMBL ID: CHEMBL403272
• Mol file: 88909-96-0.mol

Synonyms:1h,3H-benzo(de)isoquinoline-2-butyric acid-1,3-dione;isodibut;izodibut

Chemical Property of Virstatin

Chemical Property:

• Vapor Pressure: 2.42E-12mmHg at 25°C
• Boiling Point: 536.5°C at 760 mmHg
• Flash Point: 278.3°C
• PSA: 76.37000
• Density: 1.403g/cm³
• LogP: 1.81750
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 283.08445790
• Heavy Atom Count: 21
• Complexity: 431

Purity/Quality:

98%Min ^*data from raw suppliers

4-(1,3-Dioxo-1h,3h-benzo[de]isoquinolin-2-yl)-butyricacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C3C(=C1)C(=O)N(C(=O)C3=CC=C2)CCCC(=O)O
• Uses: inhibits virulence regulation in Vibrio cholerae, antiviral

Technology Process of Virstatin

There total 4 articles about Virstatin 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: 100.0%

ethyl 4-(1,3-dioxo-2,3-dihydro-1H-benzo[d,e]isoquinolin-2-yl)butanoate (150705-10-5) → 4-(1,3-dioxo-2,3-dihydro-1H-benzo[d,e]isoquinolin-2-yl)butanoic acid (88909-96-0)

Guidance literature:

With hydrogenchloride; for 6h; Heating;

DOI:10.1016/j.ejmech.2006.12.039

Reference yield: 97.0%

1,8-Naphthalic anhydride (81-84-5) + 4-amino-n-butyric acid (56-12-2) → 4-(1,3-dioxo-2,3-dihydro-1H-benzo[d,e]isoquinolin-2-yl)butanoic acid (88909-96-0)

Guidance literature:

In N,N-dimethyl-formamide; Inert atmosphere; Heating;

DOI:10.1002/ejic.201800799

Reference yield:

1,8-Naphthalimide (81-83-4) → 4-(1,3-dioxo-2,3-dihydro-1H-benzo[d,e]isoquinolin-2-yl)butanoic acid (88909-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / NaH; tetra-n-butylammonium iodide / dimethylformamide / 24 h / 20 °C

2: 100 percent / aq. hydrochloric acid / 6 h / Heating

With hydrogenchloride; tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2006.12.039

upstream raw materials:

1,8-Naphthalic anhydride

4-amino-n-butyric acid

ethyl 4-(1,3-dioxo-2,3-dihydro-1H-benzo[d,e]isoquinolin-2-yl)butanoate

1,8-Naphthalimide

Refernces

• 1、 Sarma, Rupam J.,Devi, Kakali. "Cystine-derived bis-naphthalimides as stimuli-responsive fluorescent gelators". . p. 4375 - 4383. Retrieved 2015.
• 2、 Wang, Qingpeng,Li, Guoshuai,Liu, Zhifang,Tan, Xiaoxiao,Ding, Zhuang,Ma, Jing,Li, Lanjie,Li, Dacheng,Han, Jun,Wang, Bingquan. "Naphthalimide Platinum(IV) Compounds as Antitumor Agents with Dual DNA Damage Mechanism to Overcome Cisplatin Resistance". supporting information. p. 4442 - 4451. Retrieved 2018/10/25.