Cellocidin

Base Information

• Chemical Name: Cellocidin
• CAS No.: 543-21-5
• Deprecated CAS: 102489-37-2
• Molecular Formula: C4H4 N2 O2
• Molecular Weight: 112.088
• Hs Code.: 2924199090
• European Community (EC) Number: 684-490-7
• NSC Number: 65381,38643
• UNII: 1K327HA41T
• DSSTox Substance ID: DTXSID1060261
• Nikkaji Number: J3.644G
• Wikipedia: Cellocidin
• Wikidata: Q5058318
• Metabolomics Workbench ID: 57860
• ChEMBL ID: CHEMBL1978380
• Mol file: 543-21-5.mol

Synonyms:cellocidin;cellocidin hemihydrate

Chemical Property of Cellocidin

Chemical Property:

• Vapor Pressure: 0.00167mmHg at 25°C
• Melting Point: 179 °C
• Refractive Index: 1.4610 (estimate)
• Boiling Point: 294°Cat760mmHg
• PKA: 13.01±0.50(Predicted)
• Flash Point: 131.6°C
• PSA: 86.18000
• Density: 1.41g/cm³
• LogP: -0.63900
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 112.027277375
• Heavy Atom Count: 8
• Complexity: 165

Purity/Quality:

99.9% ^*data from raw suppliers

Cellocidin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25-21
• Safety Statements: 45-36/37-28A

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(#CC(=O)N)C(=O)N
• Description: Cellocidin is an antibiotic originally isolated from S. chibaensis. It is active against various bacterial strains including M. tuberculosis and against the trypanosomes T. brucei and T. rhodesiense (IC50s = 150 and 30 ng/ml, respectively). It inhibits proliferation of LCL1 and LCL2 cells transformed by Epstein-Barr virus (EBV), activates the c-Myc and NF-κB pathways in BC3 and LCL1 cells, and induces necrotic cell death in B cells infected with gammaherpes virus. Cellocidin (100-200 ppm) is protective against bacterial leaf blight in rice plants and inhibits α-ketoglutarate oxidation in X. oryzae, the bacterium that causes leaf blight, when used at a concentration of 1 ppm, suggesting that it inhibits the citric acid cycle. Formulations containing cellocidin have been used as agricultural pesticides.
• Uses: Cellocidin is a small neutral alkyne produced by a number of Streptomyces species, first discovered by Suzuki and colleagues in 1958. Cellocidin has a broad antibacterial, antifungal and antitumor profile due to its ability to react with endogenous thiols like cysteine and glutathione. Cellocidin occurs as a weak active in many bioassays using actinomycete crude extracts and is thus a useful standard for chemical and bioassay dereplication.

Technology Process of Cellocidin

There total 4 articles about Cellocidin 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: 95.0%

dimethyl acetylenedicarboxylate (762-42-5) → Cellocidin (543-21-5)

Guidance literature:

With ammonia; at -50 ℃;

DOI:10.1016/0022-2860(93)08005-O

Reference yield:

dimethyl α,α'-difluorosuccinate (363-59-7,222312-03-0) → Cellocidin (543-21-5)

Guidance literature:

With ammonia;

Reference yield:

dimethyl α,α'-difluorosuccinate (363-59-7,222312-03-0) + ammonium hydroxide → Cellocidin (543-21-5)

Guidance literature:

upstream raw materials:

dimethyl α,α'-difluorosuccinate

dimethyl acetylenedicarboxylate

Downstream raw materials:

2-butynedinitrile

propiolonitrile

1-[2-(phenylsulfonamido)ethyl]-1H-1,2,3-triazole-4,5-dicarboxylamide

5-(4-methoxy-phenyl)-1,4,6,7,7-pentamethyl-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid diamide

Refernces

• 1、 Khlifi,Paillous,Bruston,Guillemin,Benilan,Daoudi,Raulin. "Gas infrared spectra, assignments, and absolute IR band intensities of C4N2 in the 250-3500 cm-1 region: Implications for Titan's stratosphere". . p. 707 - 712. Retrieved 2007/10/03.
• 2、 Dunn, Peter J.,Rees, Charles W.. "Organic Heterocyclothiazenes. Part 5. Cycloaddition Reactions of Tetrasulphur Tetranitride with Highly Electron Deficient Alkynes". . p. 1579 - 1584. Retrieved 2007/10/02.