N,N'-[sulfanediylbis(Ethane-2,1-Diyl-1,3,4-Thiadiazole-5,2-Diyl)]bis(2-Phenylacetamide)

Base Information

Chemical Name:N,N'-[sulfanediylbis(Ethane-2,1-Diyl-1,3,4-Thiadiazole-5,2-Diyl)]bis(2-Phenylacetamide)
CAS No.:314045-39-1
Molecular Formula:C24H24N6O2S3
Molecular Weight:524.692
Hs Code.:2934999090
European Community (EC) Number:803-573-2
Nikkaji Number:J2.510.616D
Wikidata:Q27449834
Pharos Ligand ID:11LKAFJBJS8X
ChEMBL ID:CHEMBL2177757
Mol file:314045-39-1.mol

Synonyms:BPTES;314045-39-1;Bis-2-(5-phenylacetamido-1,3,4-thiadiazol-2-yl)ethyl sulfide;N,N'-[sulfanediylbis(Ethane-2,1-Diyl-1,3,4-Thiadiazole-5,2-Diyl)]bis(2-Phenylacetamide);3uo9;N,N'-((thiobis(ethane-2,1-diyl))bis(1,3,4-thiadiazole-5,2-diyl))bis(2-phenylacetamide);2-phenyl-N-[5-[2-[2-[5-[(2-phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]ethylsulfanyl]ethyl]-1,3,4-thiadiazol-2-yl]acetamide;CHEMBL2177757;Glutaminase Inhibitor II, BPTES;2,2'-(5,5'-(2,2'-thiobis(ethane-2,1-diyl))bis(1,3,4-thiadiazole-5,2-diyl))bis(azanediyl)bis(1-phenylethanone);2-phenyl-N-{5-[2-({2-[5-(2-phenylacetamido)-1,3,4-thiadiazol-2-yl]ethyl}sulfanyl)ethyl]-1,3,4-thiadiazol-2-yl}acetamide;4jkt;04A;SCHEMBL2640644;SNX1770;HMS3866K13;BCP15991;BPTES, >=95% (HPLC);EX-A2297;SNX-1770;BDBM50400050;MFCD01079848;NSC798303;s7753;AKOS027470168;CCG-269883;CS-4586;NSC-798303;NCGC00420698-04;AC-29967;AS-70948;HY-12683;A14954;EN300-127250;US8604016, 1;Q27449834;Z1589183734;Bis[2-[5-[(2-phenylacetyl)amino]-1,3,4-thiadiazole-2-yl]ethyl] sulfide;(N,N'-[thiobis(2,1-ethanediyl-1,3,4-thiadiazole-5,2-diyl)]bisbenzeneacetamide);N,N'-[Thiobis(2,1-ethanediyl-1,3,4-thiadiazole-5,2-diyl)]bisbenzeneacetamide;N,N'-(5,5'-(2,2'-Thiobis(ethane-2,1-diyl))bis(1,3,4-thiadiazole-5,2-diyl))bis(2-phenylacetamide)

Suppliers and Price of N,N'-[sulfanediylbis(Ethane-2,1-Diyl-1,3,4-Thiadiazole-5,2-Diyl)]bis(2-Phenylacetamide)

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
BPTES
10mg
$ 115.00

TRC
BPTES
250mg
$ 1385.00

Tocris
BPTES ≥95%(HPLC)
50
$ 682.00

Tocris
BPTES ≥95%(HPLC)
10
$ 162.00

Sigma-Aldrich
Glutaminase Inhibitor II, BPTES - CAS 314045-39-1 - Calbiochem
10 mg
$ 188.00

Sigma-Aldrich
Glutaminase Inhibitor II, BPTES - CAS 314045-39-1 - Calbiochem
5300300001
$ 181.00

Sigma-Aldrich
BPTES ≥95% (HPLC)
5mg
$ 118.00

Sigma-Aldrich
BPTES ≥95% (HPLC)
25mg
$ 467.00

DC Chemicals
GlutaminaseInhibitorII,BPTES >98%
1 g
$ 1600.00

DC Chemicals
GlutaminaseInhibitorII,BPTES >98%
250 mg
$ 1000.00

Total 20 raw suppliers

Chemical Property of N,N'-[sulfanediylbis(Ethane-2,1-Diyl-1,3,4-Thiadiazole-5,2-Diyl)]bis(2-Phenylacetamide)

Chemical Property:

PKA:9.13±0.50(Predicted)
PSA：198.52000
Density:1.420±0.06 g/cm3(Predicted)
LogP:5.56940
Storage Temp.:2-8°C
Solubility.:DMSO: soluble10mg/mL, clear
XLogP3:4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:12
Exact Mass:524.11228755
Heavy Atom Count:35
Complexity:609

Purity/Quality:

99%, ^*data from raw suppliers

BPTES ^*data from reagent suppliers

Safty Information:

Pictogram(s): Xi
Hazard Codes:Xi
Statements: 36/37/38
Safety Statements: 26

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:C1=CC=C(C=C1)CC(=O)NC2=NN=C(S2)CCSCCC3=NN=C(S3)NC(=O)CC4=CC=CC=C4
Description BPTES (314045-39-1) is a potent and selective allosteric1 inhibitor of kidney-type glutaminase (GLS1), IC50 = 3.3 μM2.? Selective for GLS1 over GLS2, g-glutamyl transpeptidase and glutamate dehydrogenase. Shuts down an alternative energy-generating glutaminolysis pathway in P493 cells under both glucose deprivation or hypoxia.3 Reduces the growth of P493 cell xenografts by 50% over a 10 day treatment.4 BPTES inhibition of glutamine utilization in cancer cells increases PD-L1 expression.5 Clears senescent cells and improves various age-related disorders in a geriatric mouse model.6
Uses Bis-2-(5-phenylacetamido-1,3,4-thiadiazol-2-yl)ethyl sulfide (BPTES) has been used as a glutaminase inhibitor.

Technology Process of N,N'-[sulfanediylbis(Ethane-2,1-Diyl-1,3,4-Thiadiazole-5,2-Diyl)]bis(2-Phenylacetamide)

There total 3 articles about N,N'-[sulfanediylbis(Ethane-2,1-Diyl-1,3,4-Thiadiazole-5,2-Diyl)]bis(2-Phenylacetamide) 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: 88.0%

: 303065-25-0
5,5'-(thiobis(ethane-2,1-diyl))bis(1,3,4-thiadiazol-2-amine)

: 103-80-0
phenylacetyl chloride

: 314045-39-1
2-phenyl-N-[5-[2-[2-[5-[(2-phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]ethylsulfanyl]ethyl]-1,3,4-thiadiazol-2-yl]acetamide

Guidance literature:: With triethylamine; In N,N-dimethyl acetamide; at 20 ℃;
DOI:10.1021/jm301191p

Reference yield:

: 103-82-2
phenylacetic acid

: 303065-25-0
5,5'-(thiobis(ethane-2,1-diyl))bis(1,3,4-thiadiazol-2-amine)

: 314045-39-1
2-phenyl-N-[5-[2-[2-[5-[(2-phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]ethylsulfanyl]ethyl]-1,3,4-thiadiazol-2-yl]acetamide

Guidance literature:: With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/acs.jmedchem.8b01198

Reference yield:

: 111-17-1
4-thiaheptane-1,7-dioic acid

: 314045-39-1
2-phenyl-N-[5-[2-[2-[5-[(2-phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]ethylsulfanyl]ethyl]-1,3,4-thiadiazol-2-yl]acetamide

Guidance literature:: Multi-step reaction with 2 steps

1: trichlorophosphate / 3 h / 90 °C

2: triethylamine / N,N-dimethyl acetamide / 20 °C

With triethylamine; trichlorophosphate; In N,N-dimethyl acetamide;
DOI:10.1021/jm301191p