ChemicalBook > CAS DataBase List > N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]cyclohexyl}benzenesulfonamide

N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]cyclohexyl}benzenesulfonamide

Product Name: N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]cyclohexyl}benzenesulfonamide
CAS No.: 891016-02-7
Chemical Name: N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]cyclohexyl}benzenesulfonamide
Synonyms: ML-SI3;ML-S13;CCG-143140;ML-SI3 ，E0026;CCG143140,CCG 143140;CCG-143140, 10 mM in DMSO;N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]cyclohexyl}benzenesulfonamide;Benzenesulfonamide, N-[2-[4-(2-methoxyphenyl)-1-piperazinyl]cyclohexyl]-
CBNumber: CB94774863
Molecular Formula: C23H31N3O3S
Formula Weight: 429.58
MOL File: 891016-02-7.mol

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N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]cyclohexyl}benzenesulfonamide Property

Boiling point:: 589.3±60.0 °C(Predicted)
Density: 1.26±0.1 g/cm3(Predicted)
storage temp.: Store at -20°C
solubility: DMSO : 50 mg/mL (116.39 mM; Need ultrasonic)
pka: 11.63±0.40(Predicted)
form: Solid
color: White to off-white
InChIKey: OVTXOMMQHRIKGL-UHFFFAOYSA-N
SMILES: C1(S(NC2CCCCC2N2CCN(C3=CC=CC=C3OC)CC2)(=O)=O)=CC=CC=C1

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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).

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

P362Take off contaminated clothing and wash before reuse.

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N-Bromosuccinimide Price

Matrix Scientific

Product number: 176741
Product name: N-{2-[4-(2-Methoxyphenyl)-1-piperazinyl]cyclohexyl}benzenesulfonamide
Packaging: 100mg
Price: $990
Updated: 2021/12/16

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N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]cyclohexyl}benzenesulfonamide Chemical Properties,Usage,Production

Uses

ML-SI3 is a mixture of cis/trans ML-SI3 (HY-139426A), which is a TRPML1/2 channel inhibitor with IC50s of 4.7 μM and 1.7 μM, respectively. ML-SI3 also inhibits lysosomal calcium efflux and blocks downstream TRPML1-mediated autophagy. The cis/trans ML-SI3 (HY-139426A) components of ML-SI3 are TRPML2 activators with EC50s of 3.3 μM and 9.4 μM, respectively[1][2].

Biological Activity

ML-SI3 is a 4-diastereomer racemate (2 cis and 2 trans isomers) with a cation channel TRPML1-blocking (IC50 = 3.1 μM/trans, 18.5 μM/cis against 5 μM ML-SA1-induced cellular calcium response) and TRPML2-activating activity (EC50 = 3.3 μM/trans, 9.4 μM/cis), while exhibiting much weaker TRPML3 potency (EC50 = 28.5 μM/trans, IC50 = 29.0 μM/cis). ML-SI3 is shown to compete against ML-SA1 for binding the same TRPML1 hydrophobic cavity. Comparing with ML-SI1 (GW405833), ML-SI3 is more potent and not agonist-dependent, effectively antagonizing against TRPML1 activation by both MK6-83 and ML-SA1.

in vivo

ML-SI3 (1.5 mg/kg, i.p., four times) attenuates I/R injury in mouse cardiomyocytes^[6].

Animal Model:	Myocardial Ischemia/reperfusion (I/R) injury mice^[5]
Dosage:	1.5 mg/kg
Administration:	Intraperitoneal injection (i.p.), four times before and during the in vivo I/R (ischemia 30 min and reperfusion 1 day)
Result:	Restored the blocked autophagic fux in the cardiomyocytes subjected to I/R.

IC 50

Schistosome; TRPML1: 4.7 μM (IC₅₀); TRPML2: 1.7 μM (IC₅₀); TRPML3: 12.5 μM (IC₅₀)

References

[1] Rühl P, et al. Estradiol analogs attenuate autophagy, cell migration and invasion by direct and selective inhibition of TRPML1, independent of estrogen receptors. Sci Rep. 2021 Apr 15;11(1):8313. DOI:10.1038/s41598-021-87817-4
[2] Leser C, et al. Chemical and pharmacological characterization of the TRPML calcium channel blockers ML-SI1 and ML-SI3. Eur J Med Chem. 2021 Jan 15;210:112966. DOI:10.1016/j.ejmech.2020.112966
[3] Kilpatrick BS, et al. Endo-lysosomal TRP mucolipin-1 channels trigger global ER Ca2+ release and Ca2+ influx. J Cell Sci. 2016 Oct 15;129(20):3859-3867. DOI:10.1242/jcs.190322
[4] Bais S, et al. Schistosome TRPML channels play a role in neuromuscular activity and tegumental integrity. Biochimie. 2022 Mar;194:108-117. DOI:10.1016/j.biochi.2021.12.018
[5] Zhang X, et al. Rapamycin directly activates lysosomal mucolipin TRP channels independent of mTOR. PLoS Biol. 2019 May 21;17(5):e3000252. DOI:10.1371/journal.pbio.3000252
[6] Xing Y, et al. Blunting TRPML1 channels protects myocardial ischemia/reperfusion injury by restoring impaired cardiomyocyte autophagy. Basic Res Cardiol. 2022 Apr 7;117(1):20. DOI:10.1007/s00395-022-00930-x

N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]cyclohexyl}benzenesulfonamide Preparation Products And Raw materials

Raw materials

Preparation Products

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891016-02-7, N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]cyclohexyl}benzenesulfonamideRelated Search:

N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]cyclohexyl}benzenesulfonamide

Benzenesulfonamide, N-[2-[4-(2-methoxyphenyl)-1-piperazinyl]cyclohexyl]-

ML-SI3

CCG-143140

ML-S13

CCG143140,CCG 143140

CCG-143140, 10 mM in DMSO

ML-SI3 ，E0026

891016-02-7