ChemicalBook > CAS DataBase List > 8-[4-[4-(4-Chlorophenzyl)piperazide-1-sulfonyl)phenyl]]-1-propylxanthine

8-[4-[4-(4-Chlorophenzyl)piperazide-1-sulfonyl)phenyl]]-1-propylxanthine

Product Name
8-[4-[4-(4-Chlorophenzyl)piperazide-1-sulfonyl)phenyl]]-1-propylxanthine
CAS No.
1092351-10-4
Chemical Name
8-[4-[4-(4-Chlorophenzyl)piperazide-1-sulfonyl)phenyl]]-1-propylxanthine
Synonyms
PSB 603;PSB-603 >=98% (HPLC);8-[4-[4-(4-Chlorophenzyl)piperazide-1-sulfonyl)phenyl]]-1-propylxanthine;1H-Purine-2,6-dione, 8-[4-[[4-(4-chlorophenyl)-1-piperazinyl]sulfonyl]phenyl]-3,9-dihydro-1-propyl-;8-(4-{[4-(4-chlorophenyl)piperazin-1-yl]sulfonyl}phenyl)-1-propyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
CBNumber
CB32518737
Molecular Formula
C24H25ClN6O4S
Formula Weight
529.01
MOL File
1092351-10-4.mol
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8-[4-[4-(4-Chlorophenzyl)piperazide-1-sulfonyl)phenyl]]-1-propylxanthine Property

Melting point:
>298 °C (decomp)
Density 
1.430±0.06 g/cm3(Predicted)
storage temp. 
Store at +4°C
solubility 
Soluble to 50 mM in DMSO
form 
Powder
pka
7.37±0.70(Predicted)
color 
Off-white to light brown
InChIKey
OVHCTHHFOHMNFV-UHFFFAOYSA-N
SMILES
O=C(N1CCC)NC2=C(N=C(C3=CC=C(S(=O)(N4CCN(C5=CC=C(Cl)C=C5)CC4)=O)C=C3)N2)C1=O
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Safety

WGK Germany 
WGK 3
Storage Class
11 - Combustible Solids
Hazard Classifications
Skin Irrit. 2
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML1983
Product name
PSB-603
Purity
≥98% (HPLC)
Packaging
5mg
Price
$145
Updated
2026/03/19
Sigma-Aldrich
Product number
SML1983
Product name
PSB-603
Purity
≥98% (HPLC)
Packaging
25mg
Price
$584
Updated
2026/03/19
Cayman Chemical
Product number
25637
Product name
PSB-603
Purity
≥98%
Packaging
1mg
Price
$38
Updated
2024/03/01
Cayman Chemical
Product number
25637
Product name
PSB-603
Purity
≥98%
Packaging
5mg
Price
$121
Updated
2024/03/01
Cayman Chemical
Product number
25637
Product name
PSB-603
Purity
≥98%
Packaging
10mg
Price
$223
Updated
2024/03/01
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8-[4-[4-(4-Chlorophenzyl)piperazide-1-sulfonyl)phenyl]]-1-propylxanthine Chemical Properties,Usage,Production

Uses

PSB-603 is a potent and highly selective A2B adenosine receptor antagonist exhibiting a Ki value of 0.553 nM and virtually no affinity for the human and rat A1 and A2A and the human A3 receptors up to a concentration of 10 μM[1].

Biological Activity

PSB-603 is an adenosine receptor A2b antagonist (IC50 = 1.13 nM against 10 μM A2bR agonist NECA-induced calcium response in Jurk at T cells in the presence of 200 nM A2aR antagonist MSX-2) th at targets A2bR with high affinity (KD = 0.403 nM/human, 0.457 nM/rat, 4.09 nM/mouse A2bR; Ki against 0.3 nM [3H]PSB-603 = 0.553 nM/human, 0.355 nM/rat, 0.265 nM/mouse A2bR) and selectivity, exhibiting little affinity toward A1, A2a, or A3 adenosine receptors by competition binding assay (Ki >10 μM against 0.4 nM [3H]DPCPX for human/r at A1R, 1 nM [3H]MSX-2 for human/mouse/r at A2aR, 10 nM [3H]NECA for human/mouse/r at A3R) with the exception of mouse A1R (Ki = 42.2 nM against 0.4 nM [3H]DPCPX).', 'PSB-603 is known to modify cellular metabolism and enhance cellular sensitivity for chemotherapy. Thus, PSB-603 is recognized to possess anticancer action, which has been studied in colorectal cancer.

in vivo

PSB-603 shows anti-inflammatory effect in local and systemic inflammation models. PSB-603 (5 mg/kg b.w. ip) significantly reduces inflammation in two mice models of inflammation (local and systemic). PSB-603 significantly decreases levels of the inflammatory cytokines IL-6, TNF-α and of ROS in the inflamed paw and reduces inflammation of the peritoneum by significantly decreasing the infiltration of leukocytes[4]. PSB-603 is administered as suspensions in 1 % Tween 80[4].

Animal Model:Adult male Albino Swiss mice, CD-1, weighing 25-30 g[4]
Dosage:1, 5 or 10 mg/kg
Administration:Administered intraperitoneally (ip), prior to carrageenan injection
Result:Carrageenan-induced edema model. The increase in paw oedema was significantly inhibited in all groups receiving PSB-603. The dose of 5 mg/kg turned out to be the most active.

storage

Store at +4°C

References

[1] Thomas Borrmann, et al. 1-alkyl-8-(piperazine-1-sulfonyl)phenylxanthines: development and characterization of adenosine A2B receptor antagonists and a new radioligand with subnanomolar affinity and subtype specificity. J Med Chem. 2009 Jul 9;52(13):3994-4006. DOI:10.1021/jm900413e
[2] Mohamad Wessam Alnouri, et al. Selectivity is species-dependent: Characterization of standard agonists and antagonists at human, rat, and mouse adenosine receptors. Purinergic Signal. 2015 Sep;11(3):389-407. DOI:10.1007/s11302-015-9460-9
[3] Nadine Borg, et al. CD73 on T Cells Orchestrates Cardiac Wound Healing After Myocardial Infarction by Purinergic Metabolic Reprogramming. Circulation. 2017 Jul 18;136(3):297-313. DOI:10.1161/CIRCULATIONAHA.116.023365
[4] Magdalena Kotańska, et al. PSB 603 - a known selective adenosine A2B receptor antagonist-has anti-inflammatory activity in mice. Biomed Pharmacother. 2021 Mar;135:111164. DOI:10.1016/j.biopha.2020.111164

8-[4-[4-(4-Chlorophenzyl)piperazide-1-sulfonyl)phenyl]]-1-propylxanthine Preparation Products And Raw materials

Raw materials

Preparation Products

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8-[4-[4-(4-Chlorophenzyl)piperazide-1-sulfonyl)phenyl]]-1-propylxanthine Suppliers

3B Pharmachem (Wuhan) International Co.,Ltd.
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821-50328103-801 18930552037
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3bsc@sina.com
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Shanghai Lollane Biological Technology Co.,Ltd.
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021-52996696,15000506266 15000506266
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+86-21-52996696
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EMMX Biotechnology LLC
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Tianjin Kailiqi Biotechnology Co., Ltd.
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TargetMol Chemicals Inc.
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Changzhou Chenhong Biotechnology Co., Ltd.
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ChemeGen(Shanghai) Biotechnology Co.,Ltd.
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Energy Chemical
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Shanghai Zhongzechuan Pharmaceutical Technology Co., LTD
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1092351-10-4, 8-[4-[4-(4-Chlorophenzyl)piperazide-1-sulfonyl)phenyl]]-1-propylxanthineRelated Search:


  • 8-[4-[4-(4-Chlorophenzyl)piperazide-1-sulfonyl)phenyl]]-1-propylxanthine
  • PSB 603
  • 1H-Purine-2,6-dione, 8-[4-[[4-(4-chlorophenyl)-1-piperazinyl]sulfonyl]phenyl]-3,9-dihydro-1-propyl-
  • PSB-603 >=98% (HPLC)
  • 8-(4-{[4-(4-chlorophenyl)piperazin-1-yl]sulfonyl}phenyl)-1-propyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
  • 1092351-10-4
  • C24H25ClN6O4S