110435-89-7

Upstream product

• 67-56-1 methanol 
• 586-39-0 1-nitro-3-vinyl-benzene 
• 52022-77-2 2-(3-nitrophenyl)ethanol 
• 77-78-1 dimethyl sulfate 
• 3558-60-9 1-methoxy-2-phenylethane 
• 74-88-4 methyl iodide 

Downstream Products

• 763131-61-9 N-[3-(2-methoxyethyl)phenyl]-1,2,4-benzotriazin-3-amine 1-oxide 
• 114608-73-0 3-(2-methoxyethyl)phenylamine 

Relevant academic research and scientific papers

N-Phenyl-N′-(2-chloroethyl)ureas (CEU) as potential antineoplastic agents. Part 2: Role of ω-hydroxyl group in the covalent binding to β-tubulin

Tubulin is the target of many anticancer drugs, including N-phenyl-N′-(2-chloroethyl)urea (CEU). Unlike most anti-β-tubulin agents, CEUs are protein monoalkylating agents binding through their N′-(2-chloroethyl)urea moiety to an amino acid nearby the colchicine-binding site on β-tubulin isoform-2. Following the previously synthesized and attractive N-(3-ω-hydroxyalkylphenyl)-N′-(2-chloroethyl)urea that exhibited growth inhibitory activity at the nanomolar level, we investigated the importance of lower alkyl and alkoxy groups to evaluate the effect of hydroxylated group and chain length on both cell growth inhibition and the mechanism of action of CEU. Here, we describe the preparation of two new series of CEU and show that the most potent CEU derivatives beside the ω-hydroxylated 1f were 2f and 3e, respectively. We have confirmed that the pentyl substituted CEUs 1f, 2f, and 3e are still covalently binding to β-tubulin and still arrest cell division in G2/M phase. Crown Copyright

Extravascular transport of drugs in tumor tissue: Effect of lipophilicity on diffusion of tirapazamine analogues in multicellular layer cultures

The extravascular diffusion of antitumor agents is a key determinant of their therapeutic activity, but the relationships between physicochemical properties of drugs and their extravascular transport are poorly understood. It is well-known that drug lipop

Benzoazine mono-N-oxides and benzoazine 1,4 dioxides and compositions therefrom for the therapeutic use in cancer treatments

The present invention relates to a synergetistic composition comprising one or more benzoazine-mono-N-oxides, and one or more benzoazine 1,4 dioxides for use in cancer therapy. The invention also provides a range of novel 1,2,4 benzoazine-mono-N-oxides and related analogues. These can be used as potentiators of the cytotoxicity of existing anticancer drugs and therapies for cancer treatment.

Benzoazine mono-N-oxides and benzoazine 1,4 dioxides and compositions therefrom for the therapeutic use in cancer treatments

The present invention relates to a synergetistic composition comprising one or more benzoazine-mono-N-oxides, and one or more benzoazine 1,4 dioxides for use in cancer therapy. The invention also provides a range of novel 1,2,4 benzoazine-mono-N-oxides and related analogues. These can be used as potentiators of the cytotoxicity of existing anticancer drugs and therapies for cancer treatment.

Experiments on the Chaperon effect in the nitration of aromatics

A nitro group may be effectively delivered to the ortho position of alkylbenzenes, provided that a suitable chaperon function is located in α- position and a dilute of HNO3 in CH2Cl2 is used. The carbonyl function of an aldehyde or ketone is the best choice, but a carboxyl, alkoxycarbonyl, and amide groups all work well. The ether function showed a less pronounced ortho orientation effect, whereas the hydroxyl group was too prone to oxidation. Side reactions were minimal under the conditions employed. A para chaperon effect was seemingly at work in the CH2Cl2 nitration of benzenepropanenitrile. All the results were compared with the corresponding classical nitration in H2SO4.

Ozone-mediated nitration of phenylalkyl ethers, phenylacetic esters, and related compounds with nitrogen dioxide. the highest ortho substitution observed in the electrophilic nitration of arenes

By the combined action of ozonized oxygen and nitrogen dioxide (the kyodai-nitration), the title compounds were smoothly nitrated in dichloromethane at subzero degrees with hiigh ortho positional selectivity. Although the conventional nitration of phenylacetic acid and esters mainly produces m- and p-nitro derivatives, the present nitration offers a simple high-yield synthesis of o-nitro derivatives which are important as precursor in organic synthesis. The proportions of the ortho isomer in the nitration products from methyl 2-phenylethyl ether and methyl phenylacetate were 71 and 88%, respectively, the latter value being the highest ortho isomer proportion so far observed in the electrophilic aromatic nitration. The observed high ortho selectivity has been rationalized in terms of radical cation intermediate and six-membered cyclic transition state.

Photoaddition of Water and Alcohols to 3-Nitrostyrenes. Structure-Reactivity and Solvent Effects

The photoadditions of water and several alcohols to the triplet excited states of 3-nitrostyrenes 1, 3-5, and 8 to give the corresponding anti-Markovnikov addition products are reported.Both 3- and 4-nitrostilbenes (6 and 7, respectively) do not undergo photoaddition on direct or sensitized irradiation in aqeous or alcohol solutions; only trans to cis photoisomerisation is observed.It is proposed that for the nitrostilbenes, efficient twisting of the alkene in the triplet excited state competes favorably with photoaddition.The efficient photoaddition of the water and methanol observed for 5-nitroindene (8)-the alkene moiety of which cannot attain an orthogonal ("twisted") state-is taken as additional evidence that these photoadditions probably occur via the planar triplet state and that twisting results in only deactivation to the ground state.The use of cosolvents (CH3CN and HCONH2) on several photoadditions is also reported.For example, use of CH3CN cosolvent in aqueous solution decreases the efficiency of photohydration in the parent 3-nitrostyrene (1) but is observed to enhance the efficiency of reaction (until about 40-70 mol percent CH3CN, depending on the substrate) for 3, 4, and 8.Quantum yields for photohydration and photoaddition of alcohols are reported for several systems.

ENHANCED NUCLEOPHILE SELECTIVITY IN THE PHOTOADDITION TO STYRENE. COMPARISON WITH THE THERMAL ADDITION

The reactivity-selectivity properties of the sec-phenethyl carbenium ion and its analogues have been examined in binary-aqueous solutions of alcohols (ROH; R = Me, Et, CF3CH2, n-Bu, t-Bu, n-Pr, i-Pr), acetic acid, and in solutions containig external nucleophiles such as thiophenol, ethanethiol, acetate, and benzenesulfinate.Selectivity (S = k(Nuc)/k(H2O) is observed to be a function of the nucleophile, the ring substituent, thermal or photochemical conditions, irradiation time, and medium acidity.In the case of styrene, the photochemically generated (usually 254 nm, 1 h) species exhibits greater selectivity (up to two orders of magnitude) than its thermal counterpart, generated (usually 80 deg C, 2-4 d) in identical media, particularly in aqueous-rich solvent compositions.A rationale for these differences, supported by fluorescence quenching experiments, and the other effects upon selectivity will be discussed.