Tasisulam

Base Information

• Chemical Name: Tasisulam
• CAS No.: 519055-62-0
• Molecular Formula: C11H6BrCl2NO3S2
• Molecular Weight: 415.116
• Hs Code.: 2934999090
• UNII: 1YC4W9MSLJ
• DSSTox Substance ID: DTXSID20199869
• Nikkaji Number: J2.407.374B
• Wikidata: Q27253184
• NCI Thesaurus Code: C62794
• Metabolomics Workbench ID: 153016
• ChEMBL ID: CHEMBL2110587
• Mol file: 519055-62-0.mol

Synonyms:LY 573636;LY-573636;LY573636;LY573636 sodium;N-((5-bromo-2-thienyl)sulfonyl)-2,4-dichlorobenzamide;tasisulam

Chemical Property of Tasisulam

Chemical Property:

• PKA: 3.45±0.10(Predicted)
• PSA: 99.86000
• Density: 1.813 g/cm³
• LogP: 5.40780
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 412.83495
• Heavy Atom Count: 20
• Complexity: 471

Purity/Quality:

99% ^*data from raw suppliers

Tasisulam ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1Cl)Cl)C(=O)NS(=O)(=O)C2=CC=C(S2)Br
• Recent ClinicalTrials: A Tasisulam and Midazolam Drug Interaction Study in Cancer Patients
• Recent EU Clinical Trials: A Randomized Phase 3 Study of Tasisulam Administered as an Intravenous Infusion on Day 1 of a 28-Day Cycle vs. Paclitaxel as Second-Line Treatment in Patients with Metastatic Melanoma
• Uses: The sodium salt of Tasisulam has potential antineoplastic activity. Selectively toxic towards tumor cells, tasisulam appears to induce tumor cell apoptosis by a mitochondrial-targeted mechanism involving the loss of mitochondrial membrane potential and induction of reactive oxygen species (ROS).

Technology Process of Tasisulam

There total 5 articles about Tasisulam 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: 97.0%

2,4 dichlorobenzoic acid (50-84-0) + 2-bromothiophene-5-sulfonyl azide (1152981-12-8) → 2,4-dichloro-N-[(5-bromo-2-thienyl)sulfonyl]benzenecarboxamide (519055-62-0)

Guidance literature:

With 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane; triethylamine; In chlorobenzene; at 20 - 130 ℃; for 12h; chemoselective reaction;

DOI:10.1002/chem.201201773

Reference yield: 93.9%

5-bromo-thiophene-2-sulfonamide (53595-65-6) + 2,4-dichlorobenzoyl chloride (89-75-8) → 2,4-dichloro-N-[(5-bromo-2-thienyl)sulfonyl]benzenecarboxamide (519055-62-0)

Guidance literature:

With dmap; triethylamine; In Isopropyl acetate; at 50 - 60 ℃; for 2h; Inert atmosphere;

DOI:10.1021/op800210x

Reference yield: 87.0%

5-bromo-thiophene-2-sulfonamide (53595-65-6) + 2,4-dichlorobenzaldeyhde (874-42-0) → 2,4-dichloro-N-[(5-bromo-2-thienyl)sulfonyl]benzenecarboxamide (519055-62-0)

Guidance literature:

With 2-mesityl-2,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]triazolium chloride; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; potassium tert-butylate; In tetrahydrofuran; at 25 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.joc.7b00457

upstream raw materials:

5-bromo-thiophene-2-sulfonamide

2,4 dichlorobenzoic acid

2,4-dichlorobenzoyl chloride

2-bromothiophene-5-sulfonyl azide

Downstream raw materials:

N,N'-bis(5-bromothiophen-2-ylsulfonyl)-2,4-dichlorobenzimidamide

Refernces

• 1、 Chen, Ling,Luo, Guanglin. "Facile synthesis of acyl sulfonamides from carboxyic acids using the Mukaiyama reagent". . p. 268 - 271. Retrieved 2019/01/04.
• 2、 Fang, Yue,Gu, Zheng-Yang,Wang, Shun-Yi,Yang, Jin-Ming,Ji, Shun-Jun. "Co-Catalyzed Synthesis of N-Sulfonylcarboxamides from Carboxylic Acids and Sulfonyl Azides". . p. 9364 - 9369. Retrieved 2018/07/09.