36640-39-8

Usage

Uses

Used in Recreational Drug Industry:
JWH-018 is utilized as a recreational drug, often marketed under the monikers "Spice" or "K2". It is typically consumed via smoking for its euphoric and psychoactive properties, providing users with an experience similar to that of marijuana.
However, it is important to note that JWH-018 is associated with a variety of negative health effects, including the potential for addiction and adverse psychiatric reactions. Due to these risks and its potential for abuse, JWH-018 is classified as a controlled substance in many jurisdictions, indicating a need for caution and regulation in its use.

InChI:InChI=1/C16H13ClN2O/c17-14-8-6-12(7-9-14)16-13(11-20)10-19(18-16)15-4-2-1-3-5-15/h1-10,20H,11H2

Upstream product

• 36663-00-0 1-phenyl-3-(4-chlorophenyl)-4-pyrazolecarboxaldehyde 
• 99-91-2 para-chloroacetophenone 
• 100-63-0 phenylhydrazine 
• 57845-08-6 p-chloroacetophenone phenylhydrazone 
• 59-88-1 phenylhydrazine hydrochloride 

Downstream Products

• 55432-07-0 1-phenyl-3-(p-chlorophenyl)-pyrazol-4-acetonitrile 
• 53808-88-1 lonazolac 
• 36663-00-0 1-phenyl-3-(4-chlorophenyl)-4-pyrazolecarboxaldehyde 
• 55432-06-9 4-(chloromethyl)-3-(4-chlorophenyl)-1-phenyl-1H-pyrazole 

Relevant academic research and scientific papers

Synthesis, pharmacological activities and molecular docking studies of pyrazolyltriazoles as anti-bacterial and anti-inflammatory agents

A series of novel pyrazolyl alcohols (5a-h), pyrazolyl azides (6a-h), and pyrazolyltriazoles (8a-h, 10a-p and 12a-l) were prepared and evaluated for their bioactivity (anti-bacterial and anti-inflammatory) profile. The compound 5c displayed the potent anti-bacterial activity against Micrococcus luteus (MIC 3.9 and MBC 7.81 μg/mL). In vitro anti-inflammatory activity data denoted that compound 8b is effective among the tested compounds against IL-6 (IC50 6.23 μM). Docking analysis of compounds 5f, 8a-b, 8e-f and 8h displayed high binding energies for the compounds 8a-b and 8h towards TNF-α dimer (2AZ5 protein) and IL-6 (1ALU protein). In vivo anti-inflammatory activity of compounds 8b and 8h with respect to LPS induced mice model indicated that compound 8h showed significant reduction in TNF-α.

Novel Aryl Substituted Pyrazoles as Small Molecule Inhibitors of Cytochrome P450 CYP121A1: Synthesis and Antimycobacterial Evaluation

Three series of biarylpyrazole imidazole and triazoles are described, which vary in the linker between the biaryl pyrazole and imidazole/triazole group. The imidazole and triazole series with the short -CH2- linker displayed promising antimycobacterial activity, with the imidazole-CH2- series (7) showing low MIC values (6.25-25 μg/mL), which was also influenced by lipophilicity. Extending the linker to -C(O)NH(CH2)2- resulted in a loss of antimycobacterial activity. The binding affinity of the compounds with CYP121A1 was determined by UV-visible optical titrations with KD values of 2.63, 35.6, and 290 μM, respectively, for the tightest binding compounds 7e, 8b, and 13d from their respective series. Both binding affinity assays and docking studies of the CYP121A1 inhibitors suggest type II indirect binding through interstitial water molecules, with key binding residues Thr77, Val78, Val82, Val83, Met86, Ser237, Gln385, and Arg386, comparable with the binding interactions observed with fluconazole and the natural substrate dicyclotyrosine.

Synthesis, molecular modeling and biological evaluation of cinnamic acid derivatives with pyrazole moieties as novel anticancer agents

A series of pyrazole derivatives (1e-30e) has been designed and synthesized, and their biological activities were evaluated for EGFR and HER-2 inhibition and tumor cell antiproliferation. Among the compounds synthesized, compound 30e exhibited excellent enzyme inhibitory activity (IC50 = 0.21 ± 0.05 μM for EGFR and IC50 = 1.08 ± 0.15 μM for HER-2). Compound 30e also showed the most potent antiproliferative activity, which inhibited the growth of MCF-7 and B16-F10 cell lines with IC50 values of 0.30 ± 0.04 and 0.44 ± 0.05 μM, respectively. The molecular docking study was performed to analyze the probable binding models and the 3D-QSAR models were built for the rational design of EGFR/HER-2 inhibitors. Based on the results obtained, compound 30e with potent EGFR and HER-2 inhibitory activity may be a potential anticancer agent. the Partner Organisations 2014.

Design, synthesis and biological evaluation of (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives as potential BRAFV600E inhibitors

A series of (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives (6a-10d) were designed, synthesized and evaluated as BRAFV600E inhibitors. Biological evaluation assays indicated that compound 10a showed the most potent inhibitory activity against A375, WM266.4 and BRAFV600Ein vitro with IC50 values of 1.36 μM, 0.94 μM and 0.11 μM respectively compared with the positive compound vemurafenib. Furthermore, compound 10a showed highly selective BRAFV600E inhibitory activity in vitro. A docking simulation displayed that compound 10a could tightly bind the crystal structure of BRAFV600E at the active site. 3D-QSAR would provide a guideline to design and optimize more potent and positive BRAFV600E inhibitors based on the (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives skeleton.

A mild procedure for the preparation of 3-aryl-4-formylpyrazoles

A variety of 3-aryl-4-formylpyrazoles can be easily prepared in good yields from the corresponding methyl ketones, upon treatment with 2,4,6-trichloro[1,3, 5]triazine in N,N-dimethyl formamide at room temperature. This kind of pyrazole can constitute new building blocks for combinatorial chemistry.

4-Functionally substituted 3-heterylpyrazoles: VIII. 3-Aryl(heteryl)-4-hydroxyl(chloro)methylpyrazoles

3-Aryl(heteryl)pyrazole-4-carbaldehydes were reduced with sodium tetrahydridoborate under mild conditions to give 3-aryl(heteryl)-4-hydroxymethylpyrazoles which were converted into the corresponding 4-chloromethyl derivatives by treatment with thionyl chloride. The subsequent reaction with triphenylphosphine led to formation of triphenyl(4-pyrazolylmethyl)phosphonium chlorides, and Wittig reaction of the latter with aromatic or heteroaromatic aldehydes yielded 4-[2-aryl(heteryl)ethenyl]pyrazoles.

Synthesis and physico-chemical properties of lonazolac-Ca, a new anti-inflammatory/antirheumatic agent

Calcium-[3-(p-chlorophenyl)-1-phenylpyrazole-4]-acetate (Lonazolac-Ca, active principle of Irritren) is a new anti-inflammatory/antirheumatic agent whose synthesis and physico-chemical properties are described. The physical parameters measured (pKa, partition coefficient P, saturation concentration c(s), surface activity, protein binding) are held against the corresponding values of indometacin, diclofenac, and phenylbutazone. The size of the permeability coefficient P(m) of the passive transport through artificial phospholipid collodion membranens as well as the invasion curves calculated from P(m) indicate a good absorption of lonazolac in man.

Pyrazol-4-acetic acid compounds

Pyrazol-4-acetic acid compounds, such as substituted pyrazol-4-acetic acid, its esters, amides, nitriles and their pharamaceutically acceptable salts and method for the preparation of these compounds are disclosed. The novel compounds are useful analgesics, anti-inflammatory, and antipyretics.

1,3-Diaryl-pyrazol-4-acrylic acid and derivatives

The invention concerns diarylpyrazole lower alkanoic acids and derivatives which are pharmacologically efficacious as anti-inflammatory agents. The said compounds can be represented by the formula STR1 in which one of D, E, F and G represents hydrogen, one is a lower aliphatic acid radical or derivative thereof and the remaining two of D, E, F and G are aryl or heteroaryl radicals.