RQ-00203078

Base Information

• Chemical Name: RQ-00203078
• CAS No.: 1254205-52-1
• Molecular Formula: C₂₁H₁₃ClF₆N₂O₅S
• Molecular Weight: 554.854
• Mol file: 1254205-52-1.mol

Synonyms:RQ-00203078

Chemical Property of RQ-00203078

Chemical Property:

• Boiling Point: 602.0±65.0 °C(Predicted)
• PKA: 3.39±0.10(Predicted)
• Density: 1.588±0.06 g/cm3(Predicted)
• Solubility.: insoluble in H2O; ≥18.85 mg/mL in DMSO; ≥27.25 mg/mL in EtOH

Purity/Quality:

99%+, ^*data from raw suppliers

RQ 00203078 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: RQ-00203078 is a selective antagonist of transient receptor potential melastatin 8 (TRPM8; IC50s = 8.3 and 5.8 nM in human and rat, respectively), while having little inhibitory action against TRPV1 (IC50 > 30 μM), TRPA1 (IC50 > 10 μM), TRPV4 (IC50 = 10 μM), or TRPM2 channels (IC50 > 10 μM). It attenuates icilin-induced wet-dog shakes in rats (ED50 = 0.65 mg/kg) after oral administration. RQ-00203078 has been shown to reduce HSC3 and HSC4 oral squamous carcinoma cell migration and invasion in vitro. TRPM8, a member of the TRP melastatin subgroup, plays a role in cold hyperalgesia and cold allodynia caused by disease conditions such as chemotherapy-induced peripheral neuropathy, diabetic neuropathy, migraine, and overactive bladder. It is also known to be involved in the tumor progression of certain carcinomas.
• Uses: RQ 00203078 is a selective and orally active TRPM8 antagonist.

Technology Process of RQ-00203078

There total 6 articles about RQ-00203078 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:

methyl 4-(N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-N-(4-(trifluoromethoxy)benzyl)sulfamoyl)benzoate (1254207-09-4) → RQ-00203078 (1254205-52-1)

Guidance literature:

methyl 4-(N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-N-(4-(trifluoromethoxy)benzyl)sulfamoyl)benzoate; With water; sodium hydroxide; In tetrahydrofuran; at 18 - 50 ℃;

With hydrogenchloride; In tetrahydrofuran; water;

Reference yield:

C23H16ClF6NO5S → RQ-00203078 (1254205-52-1)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 50 ℃;

DOI:10.1016/j.bmcl.2014.10.074

Reference yield:

4-chlorosulfonyl-benzoic acid methyl ester (69812-51-7) → RQ-00203078 (1254205-52-1)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / tetrahydrofuran / 0 - 20 °C

2: caesium carbonate; sodium iodide / N,N-dimethyl-formamide / 80 °C

3: water; sodium hydroxide / tetrahydrofuran / 50 °C

With water; sodium hydride; caesium carbonate; sodium iodide; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2014.10.074

upstream raw materials:

methyl 4-(N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-N-(4-(trifluoromethoxy)benzyl)sulfamoyl)benzoate

4-(trifluoromethoxy)benzyl amine

4-chlorosulfonyl-benzoic acid methyl ester

methyl 4-(N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)sulfamoyl)benzoate

Refernces

• 1、 -. "SULFAMOYL BENZOIC ACID DERIVATIVES AS TRPM8 ANTAGONISTS". Page/Page column 47. . Retrieved 2010/11/17.