51116-22-4

Upstream product

• 120-57-0 piperonal 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 139-85-5 3,4-dihydroxybenzaldehyde 

Downstream Products

• 76934-56-0 (2-Benzo[1,3]dioxol-5-yl-cyclopropyl)-(3,4-dimethoxy-phenyl)-methanone 
• 142608-93-3 3-(benzo[d][1,3]dioxol-5-yl)-1-(2,4-dimethoxyphenyl)propan-1-one 
• 51116-23-5 2-benzo[1,3]dioxol-5-yl-4-(3,4-dimethoxy-phenyl)-4-oxo-butyronitrile 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 1198088-67-3 6-(3,4-dimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-1H-pyridin-2-one 
• 169804-26-6 2-Benzo[1,3]dioxol-5-yl-4-(3,4-dimethoxy-phenyl)-4-oxo-butyric acid methyl ester 

Relevant academic research and scientific papers

Synthesis of some novel pyrazoline-thiazole hybrids and their antimicrobial activities

A series of novel thiazolyl pyrazolines 7a-h, 9a-f, and 11a-f have been synthesized by the reaction of thioamide derivatives 5a,b with 1-aryl-2-bromoethanones 6a-d, chloroacetones 8a-c, and hydrazonoyl chlorides 10a-c. Additionally, pyrazoles 15a-c and 20 were prepared starting from enaminone 13. These newly synthesized compounds were screened for their in vitro antibacterial activity against four bacterial species. Compound 11b showed a moderate activity against Klebsiella pneumoniae. Compounds 7c and 11c revealed a moderate activity against Pseudomonas aeruginosa. In addition, the antifungal activity of the newly synthesized compounds was determined against five fungal strains. Compounds 7e, 7g, and 11e showed a good activity against Aspergillus flavus and Penicillium expansum.

An expedient, one-pot, stepwise sequential approach for the regioselective synthesis of pyrazolines

An efficient approach for the synthesis of pyrazoline/pyrazole-tethered pyridinyl methanones is described via a one-pot, stepwise, sequential methodology using chalcones and pyridine-4-carbohydrazide as substrates through a Michael addition followed by cy

Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors

Cancer is a disease characterized by the continuous growth of cells without adherence to the rules that healthy normal cells obey. Carbonic anhydrase I and II (CA I and CA II) inhibitors are used for the treatment of some diseases. The available drugs in the market have limitations or side effects, which bring about the need to develop new drug candidate compound(s) to overcome the problems at issue. In this study, new pyrazole-sulphonamide hybrid compounds 4-[5-(1,3-benzodioxol-5-yl)-3-aryl-4,5-dihydro-1Hpyrazol- 1-yl]benzenesulphonamides (4a - 4j) were designed to discover new drug candidate compounds. The compounds 4a - 4j were synthesized and their chemical structures were confirmed using spectral techniques. The hypothesis tested was whether an introduction of methoxy and polymethoxy group(s) lead to an increased potency selectivity expression (PSE) value of the compound, which reflects cytotoxicity and selectivity of the compounds. The cytotoxicity of the compounds towards tumor cell lines were in the range of 6.7 - 400 μM. The compounds 4i (PSE2 = 461.5) and 4g (PSE1 = 193.2) had the highest PSE values in cytotoxicity assays. Ki values of the compounds were in the range of 59.8 ± 3.0 - 12.7 ± 1.7 nM towards hCA I and in the range of 24.1 ± 7.1 - 6.9 ± 1.5 nM towards hCA II. While the compounds 4b, 4f, 4g, and 4i showed promising cytotoxic effects, the compounds 4c and 4g had the inhibitory potency towards hCA I and hCA II, respectively. These compounds can be considered as lead compounds for further research.

The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells

As part of a programme to develop anticancer prodrugs which are activated by cytochrome P450 (CYP)1B1, a library of 4,6-diaryl-2-pyridones was synthesised in yields of 6–60% from the corresponding chalcones. A number of these derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing little toxicity towards a non-tumour breast cell line with no CYP expression. Metabolism studies provided evidence supporting the involvement of CYP1 enzymes in the bioactivation of these compounds.

The synthesis of chalcones as anticancer prodrugs and their bioactivation in CYP1 expressing breast cancer cells

Background: Although the expression levels of many P450s differ between tumour and corresponding normal tissue, CYP1B1 is one of the few CYP subfamilies which is significantly and consistently overexpressed in tumours. CYP1B1 has been shown to be active within tumours and is capable of metabolising a structurally diverse range of anticancer drugs. Because of this, and its role in the activation of procarcinogens, CYP1B1 is seen as an important target for anticancer drug development. Objective: To synthesise a series of chalcone derivatives based on the chemopreventative agent DMU-135 and investigate their antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1. Method: A series of chalcones were synthesised in yields of 43-94% using the Claisen-Schmidt condensation reaction. These were screened using a MTT assay against a panel of breast cancer cell lines which have been characterised for CYP1 expression. Result: A number of derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing significantly lower toxicity towards a non-tumour breast cell line with no CYP expression. Experiments using the CYP1 inhibitors acacetin and α-naphthoflavone provided supporting evidence for the involvement of CYP1 enzymes in the bioactivation of these compounds. Conclusion: Chalcones show promise as anticancer agents with evidence suggesting that CYP1 activation of these compounds may be involved.

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.

Novel Compounds

A compound for use in the treatment of proliferative disorders, such as cancer, having the following formula: wherein: R1, R2 and R3 are independently H or lower alkyl; R4, R5, R6, R7 and R8 are independently H, halo, lower alkyl or —O-lower alkyl, provided that at least one is —O-lower alkyl; or at least one pair of R4 to R8, the members of which pair are adjacent to one another on the ring, are conjoined to form —O—(CR14R15)n—O—, where n is 1 or 2 and R14 and R15 are independently H or lower alkyl, and the remainder of R4 to R8 are independently H, halo, lower alkyl or —O-lower alkyl; and R9, R10, R11, R12 and R13 are independently H, halo, lower alkyl or —O— lower alkyl, provided that at least one is —O-lower alkyl; or at least one pair of R9 to R13, the members of which pair are adjacent to one another on the ring, are conjoined to form —O—(CR16R17)m—O—, where m is 1 or 2 and R16 and R17 are independently H or lower alkyl, and the remainder of R9 to R13 are independently H, halo, lower alkyl or —O-lower alkyl.

4, 6-DIPHENYLPYRID-2-0NES AGAINST CANCER

A compound for use in the treatment of proliferative disorders, such as cancer, having the following formula:z wherein: R1, R2 and R3 are independently H or lower alkyl; R4, R5, R6, R7 and R8 are independently H, halo, lower alkyl or -O-lower alkyl, provided that at least one is -O-lower alkyl; or at least one pair of R4 to R8, the members of which pair are adjacent to one another on the ring, are conjoined to form-0-(CR14R15)n-O-, where n is 1 or 2 and R14 and R15 are independently H or lower alkyl, and the remainder of R4 to R8 are independently H, halo, lower alkyl or -O-lower alkyl; and R9, R10, R11, R12 and R13 are independently H, halo, lower alkyl or -O-lower alkyl, provided that at least one is -O-lower alkyl; or at least one pair of R9 to R13, the members of which pair are adjacent to one another on the ring, are conjoined to form-O-(CR16R17)m-O-, where m is 1 or 2 and R16 and R17 are independently H or lower alkyl, and the remainder of R9 to R13 are independently H, halo, lower alkyl or -O-lower alkyl.

Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA

In the search for lead compounds for new drugs for tuberculosis, the activity of 38 synthetic chalcones were assayed for their potential inhibitory action towards a protein tyrosine phosphatase from Mycobacterium tuberculosis - PtpA. The compounds were ob

Synthesis and biological evaluation of aromatic enones related to curcumin

Curcumin, a natural product isolated from the spice turmeric, has been shown to exhibit a wide range of pharmacological activities including certain anti-cancer properties. It has been specifically shown to be an effective inhibitor of angiogenesis both in vitro and in vivo. Using curcumin as a lead compound for anti-angiogenic analog design, a series of structurally related compounds utilizing a substituted chalcone backbone have been synthesized and tested via an established SVR cell proliferation assay. The results have yielded a wide range of compounds that equal or exceed curcumin's ability to inhibit endothelial cell growth in vitro. Due to both their commercial availability and their fairly straightforward synthetic preparation, these low molecular weight compounds are attractive leads for developing future angiogenic inhibitors.