15256-07-2

Usage

Uses

Used in Organic Synthesis:
1-[(Ammoniooxy)methyl]-3-(trifluoromethyl)benzene chloride is used as a reagent in organic synthesis for its ability to facilitate the formation of various complex organic molecules. Its unique structure allows for multiple points of reactivity, making it a useful component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1-[(Ammoniooxy)methyl]-3-(trifluoromethyl)benzene chloride is employed as a building block for the synthesis of novel drug candidates. Its incorporation into molecular structures can potentially enhance the biological activity, selectivity, and pharmacokinetic properties of new compounds, contributing to the development of more effective and safer medications.
Used in Chemical Research:
1-[(Ammoniooxy)methyl]-3-(trifluoromethyl)benzene chloride is utilized in chemical research as a model compound to study reaction mechanisms, explore new synthetic methodologies, and understand the influence of structural modifications on chemical properties. Its presence in research settings aids in advancing the fundamental knowledge of organic and medicinal chemistry.

InChI:InChI=1/C8H9F3NO.ClH/c9-8(10,11)7-3-1-2-6(4-7)5-13-12;/h1-4H,5H2,12H3;1H/q+1;/p-1

Upstream product

• 705-29-3 3-Trifluoromethylbenzyl chloride 
• 349-75-7 3-(trifluoromethyl)benzyl alcohol 
• 30777-88-9 N-(3-trifluoromethyl-benzyloxy)-phthalimide 
• 85661-08-1 O-(3-(trifluoromethyl)benzyl)hydroxylamine 

Downstream Products

• 85661-15-0 6-(3-Trifluoromethyl-benzyloxy)-5,6,7,8-tetrahydro-pyrimido[4,5-d]pyrimidine-2,4-diamine 

Relevant academic research and scientific papers

Synthesis and anti-tumor activity evaluation of salinomycin C20-O-alkyl/benzyl oxime derivatives

Seventeen C20-O-alkyl/benzyl oxime derivatives were synthesized by a concise and effective method. Most of these derivatives showed tens to several hundred nanomolar IC50 values against HT-29 colorectal, HGC-27 gastric and MDA-MB-231 breast cancer cells, whose antiproliferative activity is 15-240 fold better than that of salinomycin. The C20-oxime etherified derivatives can coordinate potassium ions, and further adjust the cytosolic Ca2+ concentrations in HT-29 cells. The significant improvement of the potency should be attributed to the better ion binding and transport ability of the modified derivatives. In addition, the C20-O-alkyl/benzyl oxime derivatives showed much better selectivity indexes (SI) than salinomycin, indicating that they present lower neurotoxic risk.

Structure-activity relationships of pyrimidine nucleotides containing a 5′-α,β-methylene diphosphonate at the P2Y6 receptor

The Gq-coupled P2Y6 receptor (P2Y6R) is a component of the purinergic signaling system and functions in inflammatory, cardiovascular and metabolic processes. UDP, the native P2Y6R agonist and P2Y14R partial agonist, is subject to hydrolysis by ectonucleotidases. Therefore, we have synthesized UDP/CDP analogues containing a stabilizing α,β-methylene bridge as P2Y6R agonists and identified compatible affinity-enhancing pyrimidine modifications. A distal binding region on the receptor was explored with 4-benzyloxyimino cytidine 5′-diphosphate analogues and their potency determined in a calcium mobilization assay. A 4-trifluoromethyl-benzyloxyimino substituent in 25 provided the highest human P2Y6R potency (MRS4554, 0.57 μM), and a 5-fluoro substitution of the cytosine ring in 28 similarly enhanced potency, with >175- and 39-fold selectivity over human P2Y14R, respectively. However, 3-alkyl (31–33, 37, 38), β-D-arabinofuranose (39) and 6-aza (40) substitution prevented P2Y6R activation. Thus, we have identified new α,β-methylene bridged N4-extended CDP analogues as P2Y6R agonists that are highly selective over the P2Y14R.

O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1

Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a potent sub-micromolar inhibitor of IDO1. Structure-activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications.

ESTRATRIENE DERIVATIVES

Compounds and methods for modulating mesenchymal cell function, for instance smooth muscle and fibroblast proliferation or cytokine expression, and for treating conditions associated with mesenchymal cell function, for instance airway hyperresponsiveness

Phenoxypropoxybiguanides, prodrugs of DHFR-inhibiting diaminotriazine antimalarials

A total of 34 analogues of the biguanide PS-15 (5s), a prodrug of the diaminotriazine WR-99210 (8s), have been prepared. Several of them, such as 5b (PS-33) and 5m (PS-26), maintain or exceed the in vivo activity of PS-15 while not requiring the use of highly regulated starting materials. The putative diaminotriazine metabolites of these new analogues (compounds 8) have also been prepared and shown to maintain the activity against resistant P. falciparum strains. The structure-activity relationships of biguanides 5 and putative metabolites 8 are discussed.

Insecticidal substituted-2,4-diamino-5,6,7,8-tetrahydroquinazolines

There is provided an insecticidal composition comprising, in admixture with an agriculturally acceptable carrier, an insecticidally effective amount of a tetrahydroquinazoline compound of the formula STR1 wherein R, R1, R2, R3, R5, R6, R7, R8, and R9 are as defined herein, and methods of using the same. Certain novel substituted-phenyl tetrahydroquinazoline compounds per se are also identified.