37620-38-5

Usage

Uses

Used in Perfume and Soap Industry:
Safrole is used as a fragrance ingredient in the perfume and soap industry due to its sweet, spicy odor. It imparts a pleasant scent to these products, enhancing their appeal to consumers.
Used in Chemical Synthesis:
Safrole is also used as a precursor in the synthesis of other chemicals. Its unique chemical structure allows it to be transformed into various compounds, making it a valuable intermediate in chemical manufacturing processes.
However, it is important to note that safrole has been classified as a controlled substance in many countries due to its potential for abuse as a precursor to the illegal drug MDMA (ecstasy). Additionally, it has been found to have carcinogenic effects in animal studies and may also have harmful effects on the liver and kidneys. As a result, its use and production are heavily regulated to minimize the risks to human health and the environment.

Upstream product

• 120-57-0 piperonal 
• 122-00-9 para-methylacetophenone 
• 619-41-0 4-(bromoacetyl)toluene 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 29668-44-8 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde 
• 64376-20-1 3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-1-(4-methoxy-phenyl)-propenone 
• 1417658-61-7 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 
• 1443526-81-5 1-(benzo[d][1,3]dioxol-5-yl)-3-(p-tolyl)prop-2-yn-1-ol 
• 766-97-2 4-n-methylphenylacetylene 
• 495-76-1 piperonol 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 

Downstream Products

• 73910-94-8 4-benzo[1,3]dioxol-5-yl-2-(4-chloro-phenyl)-6-p-tolyl-pyridine 
• 73910-88-0 4-benzo[1,3]dioxol-5-yl-2-(3-nitro-phenyl)-6-p-tolyl-pyridine 
• 1197386-06-3 2-(p-tolylthio)-4-(benzo[d][1,3]dioxol-6-yl)-6-p-tolylpyridine-3-carbonitrile 
• 1443527-35-2 3-(benzo[d][1,3]dioxol-5-yl)-1,3-di-p-tolylpropan-1-one 
• 1443527-10-3 (S)-3-(benzo[d][1,3]dioxol-5-yl)-1,3-di-p-tolylpropan-1-one 
• 1465270-12-5 C₂₀H₁₆O₂ 
• 1465270-30-7 C₂₇H₂₂O₄S 
• 1376396-17-6 5-(benzo[d][1,3]dioxol-5-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 
• 835911-11-0 1-acetyl-5-(benzo[d][1,3]dioxol-5-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazole 
• 1376396-14-3 5-(benzo[d][1,3]dioxol-5-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde 
• 76287-93-9 5-Benzo[1,3]dioxol-5-yl-3-p-tolyl-4,5-dihydro-isoxazole 

Relevant academic research and scientific papers

Dihydropyrazole derivatives containing benzo oxygen heterocycle and sulfonamide moieties selectively and potently inhibit COX-2: Design, synthesis, and anti-colon cancer activity evaluation

Cyclooxygenase-2 (COX-2) as a rate-limiting metabolism enzyme of arachidonic acid has been found to be implicated in tumor occurrence, angiogenesis, metastasis as well as apoptosis inhibition, regarded as an attractive therapeutic target for cancer therapy. In our research, a series of dihydropyrazole derivatives containing benzo oxygen heterocycle and sulfonamide moieties were designed as highly potent and selective COX-2 inhibitors by computer-aided drug analysis of known COX-2 inhibitors. A total of 26 compounds were synthesized and evaluated COX-2 inhibition and pharmacological efficiency both in vitro and in vivo with multi-angle of view. Among them, compound 4b exhibited most excellent anti-proliferation activities against SW620 cells with IC50 of 0.86 ± 0.02 μM than Celecoxib (IC50 = 1.29 ± 0.04 μM). The results favored our rational design intention and provides compound 4b as an effective COX-2 inhibitor available for the development of colon tumor therapeutics.

Design, synthesis and biological evaluation of novel pyrazoline-containing derivatives as potential tubulin assembling inhibitors

Abstract A series of novel pyrazoline-containing derivatives (15-47) has been designed, synthesized and evaluated for their biological activities. Among them, compound 18 displayed the most potent antiproliferative activity against A549, MCF-7 and HepG-2 cells line (IC50 Combining double low line 0.07 μM, 0.05 μM, 0.03 μM, respectively) and the tubulin polymerization inhibitory activity (IC50 Combining double low line 1.88 μM), being comparable to CA-4. Furthermore, we also tested that compound 18 was a potent inducer of apoptosis in HepG-2 cells and it had cellular effects typical for microtubule interacting agents, causing accumulation of cells in the G2/M phase of the cell cycle. These studies, along with molecular docking, provided a new molecular scaffold for the further development of antitumor agents that target tubulin.

Antimycobacterial and anti-inflammatory activities of substituted chalcones focusing on an anti-tuberculosis dual treatment approach

Tuberculosis (TB) remains a serious public health problem aggravated by the emergence of M. tuberculosis (Mtb) strains resistant to multiple drugs (MDR). Delay in TB treatment, common in the MDR-TB cases, can lead to deleterious life-threatening inflammation in susceptible hyper-reactive individuals, encouraging the discovery of new anti-Mtb drugs and the use of adjunctive therapy based on anti-inflammatory interventions. In this study, a series of forty synthetic chalcones was evaluated in vitro for their anti-inflammatory and antimycobacterial properties and in silico for pharmacokinetic parameters. Seven compounds strongly inhibited NO and PGE2 production by LPS-stimulated macrophages through the specific inhibition of iNOS and COX-2 expression, respectively, with compounds 4 and 5 standing out in this respect. Four of the seven most active compounds were able to inhibit production of TNF-α and IL-1β. Chalcones that were not toxic to cultured macrophages were tested for antimycobacterial activity. Eight compounds were able to inhibit growth of the M. bovis BCG and Mtb H37Rv strains in bacterial cultures and in infected macrophages. Four of them, including compounds 4 and 5, were active against a hypervirulent clinical Mtb isolate as well. In silico analysis of ADMET properties showed that the evaluated chalcones displayed satisfactory pharmacokinetic parameters. In conclusion, the obtained data demonstrate that at least two of the studied chalcones, compounds 4 and 5, are promising antimycobacterial and anti-inflammatory agents, especially focusing on an anti-tuberculosis dual treatment approach.

Co-N-C Catalyst for C-C Coupling Reactions: On the Catalytic Performance and Active Sites

C-C bond-forming reactions are important in chemistry for construction of complex large molecules from readily available simple substrates. However, they usually involve the employment of organic halides and suffer from toxic or environmental issues. We report an efficient and environmentally benign methodology-aerobic oxidative cross-coupling of primary and secondary alcohols-to directly produce α,β-unsaturated ketones that are key intermediates for synthesis of agrochemical, pharmaceutical, and other fine chemicals. A noble-metal-free Co-N-C catalyst, derived from pyrolysis of cobalt-phenanthroline complexes on a mesoporous carbon support, is developed toward the target reactions and shows high catalytic activity (turnover frequency of 3.8 s-1 based on Co single atoms, surpassing the state of art in the literature), good recyclability, and wide applicability to diverse substrates (28 examples). The active sites in the Co-N-C catalyst are proposed to be Co single atoms bonded with N within graphitic sheets.

One-pot synthesis of multifunctionalized cyclopropanes

A facile one-step synthetic protocol toward multifunctionalized cyclopropanes 4 is developed from substituted chalcones 1 and sulfones 2 in good yields via a [2C+1C] annulation.

4,5-Dihydropyrazole derivatives containing oxygen-bearing heterocycles as potential telomerase inhibitors with anticancer activity

Telomere and telomerase were closely related to the occurrence and development of some cancers. After the key active site of telomerase was identified, to enhance the ability of dihydropyrazole derivatives to inhibit telomerase, we designed a series of novel 4,5-dihydropyrazole derivatives containing heterocyclic oxygen moiety based on previous studies. The telomerase inhibition assay showed that compound 10a displayed the most potent inhibitory activity with an IC50 value of 0.6 μM for telomerase. The antiproliferative assay showed that 10a exhibited high activity against human gastric cancer cell SGC-7901 with an IC50 value of 10.95 ± 0.60 μM. Flow cytometric analysis and western blot results showed that 10a induced both apoptosis and autophagy. A docking simulation showed that 10a could bind well to the active site of telomerase and act as a telomerase inhibitor. The 3D-QSAR model was also built to provide a more pharmacological understanding that could be used to design new agents with more potent telomerase inhibitory activity.

Gold meets rhodium: Tandem one-pot synthesis of β-disubstituted ketones via meyer-schuster rearrangement and asymmetric 1,4-addition

An asymmetric one-pot tandem Au/Rh-catalyzed synthesis of highly enantioenriched β-disubstituted ketones starting from racemic propargyl alcohols is disclosed. The compatibility of the two metal complexes (Au/Rh) and their orthogonal ligand systems (NHC/d

Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives containing benzodioxole as potential anticancer agents

A series of novel thiazolyl-pyrazoline derivatives containing benzodioxole (C1-C20) have been designed and synthesized. Among of the synthesized compounds, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-1-yl)- 4-(4-bromophenyl)thiazole (C6) displayed the most potent inhibitory activity for HER-2 (IC50 = 0.18 μM for HER-2). Antiproliferative assay results indicated that compound C6 owned high antiproliferative activity against MCF-7 and B16-F10 in vitro, with IC50 value of 0.09 and 0.12 μM, respectively, being comparable with the positive control Erlotinib. Docking simulation was further performed to determine the probable binding model. Based on the preliminary results, compound C6 with potent inhibitory activity in tumor growth would be a potential anticancer agent.

Synthesis, biological evaluation, 3D-QSAR studies of novel aryl-2H-pyrazole derivatives as telomerase inhibitors

A series of novel aryl-2H-pyrazole derivatives bearing 1,4-benzodioxan or 1,3-benzodioxole moiety were designed as potential telomerase inhibitors to enhance the ability of aryl-2H-pyrazole derivatives to inhibit telomerase, a target of anticancer. The telomerase inhibition tests showed that compound 16A displayed the most potent inhibitory activity with IC50 value of 0.9 μM for telomerase. The antiproliferative tests showed that compound 16A exhibited high activity against human gastric cancer cell SGC-7901 and human melanoma cell B16-F10 with IC50 values of 18.07 and 5.34 μM, respectively. Docking simulation showed that compound 16A could bind well with the telomerase active site and act as telomerase inhibitor. 3D-QSAR model was also built to provide more pharmacophore understanding that could be used to design new agents with more potent telomerase inhibitory activity.

A novel series of 3,4-disubstituted dihydropyrazoles: Synthesis and evaluation for MAO enzyme inhibition

In this study, the authors have designed and synthesized a novel series of 3-acyl-4-aryl-4,5-dihydropyrazoles, with the aim to obtain new potential scaffolds for the inhibition of both isoforms of monoamine oxidase.