52010-98-7

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 105, p. 7175, 1983 DOI: 10.1021/ja00362a028

Upstream product

• 626-19-7 Isophthalaldehyde 
• 626-18-6 1,3-dimethanol benzene 
• 587-04-2 m-Chlorobenzaldehyde 
• 15852-73-0 (3-Bromophenyl)methanol 
• 68-12-2 N,N-dimethyl-formamide 
• 140639-94-7 2-(3'-hydroxymethyl)phenyl-1,3-dioxolane 
• 17789-14-9 3-(1,3-dioxolan-2-yl)-phenylbromide 
• 68348-23-2 3-(1,3-dioxolan-2-yl)benzaldehyde 
• 28188-41-2 m-(bromomethyl)benzonitrile 
• 619-21-6 m-formylphenyl benzoic acid 
• 874-97-5 3-(hydroxymethyl)benzonitrile 
• 201230-82-2 carbon monoxide 
• 57455-06-8 3-iodobenzylalcohol 

Downstream Products

• 77113-66-7 (Z)-3-(3-Hydroxymethyl-phenyl)-2-methoxymethyl-acrylonitrile 
• 667419-25-2 3-formylbenzyl benzoate 
• 129747-43-9 (3-oxazol-5-yl-phenyl)methanol 
• 1198174-28-5 C₁₈H₁₄N₂O₂S 
• 1187590-64-2 C₁₉H₂₀BrN₃O 
• 1204300-29-7 3-(3,5-dimethylpyrazol-1-ylmethyl)benzaldehyde 
• 1431704-48-1 4-methoxy-N-(3-(((2-methoxyethoxy)methoxy)methyl)benzylidene)aniline 
• 1431704-52-7 (3R,4S)-3-acetoxy-4-(3-hydroxymethyl)phenyl-azetidin-2-one 
• 1431704-53-8 (3R,4S)-3-triethylsilyloxy-4-(3-triethylsilyloxymethyl)phenylazetidin-2-one 
• 1431704-54-9 (3R,4S)-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-(3-triethylsilyloxymethyl)phenylazetidin-2-one 
• 1431704-29-8 10-acetoxy-3'-debenzoyl-3'-[(3-hydroxymethyl)phenyl]docetaxel 
• 186246-13-9 3-(((2-methoxyethoxy)methoxy)methyl)benzaldehyde 
• 1295558-09-6 meso-(3-hydroxymethylphenyl)dipyrromethane 

Relevant academic research and scientific papers

Synthesis and evaluation of novel α-aminoamides containing benzoheterocyclic moiety for the treatment of pain

Novel α-aminoamide derivatives containing different benzoheterocyclics moiety were synthesized and evaluated as voltage-gated sodium ion channels blocks the treatment of pain. Compounds 6a, 6e, and 6f containing the benzofuran group displayed more potent in vivo analgesic activity than ralfinamide in both the formalin test and the writhing assay. Interestingly, they also exhibited potent in vitro anti-Nav 1.7 and anti-Nav 1.8 activity in the patch-clamp electrophysiology assay. Therefore, compounds 6a, 6e, and 6f, which have inhibitory potency for two pain-related Nav targets, could serve as new leads for the development of analgesic medicines.

Acylhydrazone neuraminidase inhibitor as well as preparation method and application thereof

The invention relates to an acylhydrazone neuraminidase inhibitor as well as a preparation method and application thereof, and the acylhydrazone neuraminidase inhibitor has a structure as shown in a general formula L. The disclosed compound is novel in structure, and experiments show that the acylhydrazone neuraminidase inhibitor has good neuraminidase inhibition activity and is expected to be used for preparing medicines for inhibiting neuraminidase activity.

Design, Synthesis, and Biological Evaluation of Novel Acylhydrazone Derivatives as Potent Neuraminidase Inhibitors

Neuraminidase (NA) is an important target for current research on anti-influenza drugs. The acylhydrazone derivatives containing the -CONHN═CH- framework have been shown to have good NA inhibitory activity. In this paper, a series of novel acylhydrazone NA inhibitors (9a-9n) were designed and synthesized, and the inhibitory activities against NA were evaluated in vitro. The NA inhibition results showed that compound 9j has the most potent inhibitory activity (IC50 = 0.6 μM) against NA, which is significantly lower than that of the positive control oseltamivir carboxylic acid (OSC) (IC50 = 17.00 μM). Molecular docking analysis indicates that the acylhydrazone group plays an important role in compound 9j, which can bind well to the residues Arg371 and Arg292 in the S1 subsite of NA. The good potency of 9j may be also ascribed to the extending of morpholinyl ring into the 430-cavity. The results of this work may contribute to the development of more potent NA inhibitors to against mutant influenza viruses.

Amide derivative containing benzoheterocycle structure, and composition and application thereof

The invention belongs to the technical field of medicines, and discloses an amide derivative containing a benzoheterocycle structure, and a composition and an application thereof. The amide derivativecontaining the benzoheterocycle structure is a compound represented by structural formula I and a nontoxic pharmaceutically acceptable salt thereof, or the amide derivative containing the benzoheterocycle structure is a compound represented by structural formula II or a nontoxic pharmaceutically acceptable salt thereof. The amide derivative containing the benzoheterocycle structure has good analgesic activity and good inhibition effect on a target sodium ion channel Nav1.7.

Novel Meta-iodobenzylguanidine-Based Copper Thiosemicarbazide-1-guanidinomethylbenzyl Anticancer Compounds Targeting Norepinephrine Transporter in Neuroblastoma

Meta-iodobenzylguanidine (MIBG) is a ligand with high affinity against norepinephrine transporter (NET) that has been used for diagnostic imaging and radionuclide therapy of NET-expressing tumors, such as neuroblastoma. We hypothesize that MIBG can be used as a ligand for development of new anticancer drugs targeting NET-expressing neuroblastoma (NB). To test our hypothesis, we synthesized two MIBG-based anticancer copper complexes [Cu(m-TSBG)2 and Cu(p-TSBG)2] by conjugation of a thiosemicarbazone copper group onto MIBG ligand. Both Cu(m-TSBG)2 and Cu(p-TSBG)2 compounds showed potent anticancer activity against NB cells (BE2C and SK-N-DZ cells). The NB-specific anticancer activity of Cu(m-TSBG)2 and Cu(p-TSBG)2 was further demonstrated by the reduced anticancer activities when nonconjugated MIBG ligand was used to competitively block binding of Cu(m-TSBG)2 or Cu(p-TSBG)2 onto NET-expressing NB cells. Both Cu(m-TSBG)2 or Cu(p-TSBG)2 compounds hold potential as promising new drugs for targeted therapy of neuroblastoma and other NET-expressing tumors.

IMMUNOPROTEASOME INHIBITORS

Provided herein are compounds, such as a compound of Formula (I), or a pharmaceutically acceptable salt thereof, that are immunoproteasome (such as LMP2 and LMP7) inhibitors. The compounds described herein can be useful for the treatment of diseases treatable by inhibition of immunoproteasomes. Also provided herein are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

A Series of Enthalpically Optimized Docetaxel Analogues Exhibiting Enhanced Antitumor Activity and Water Solubility

A dual-purpose strategy aimed at enhancing the binding affinity for microtubules and improving the water solubility of docetaxel led to the design and synthesis of a series of C-2- and C-3′-modified analogues. Both aims were realized when the C-3′ phenyl group present in docetaxel was replaced with a propargyl alcohol. The resulting compound, 3f, was able to overcome drug resistance in cultured P-gp-overexpressing tumor cells and showed greater activity than docetaxel against drug-resistant A2780/AD ovarian cancer xenografts in mice. In addition, the considerably lower hydrophobicity of 3f relative to both docetaxel and paclitaxel led to better aqueous solubility. A molecular model of tubulin-bound 3f revealed novel hydrogen-bonding interactions between the propargyl alcohol and the polar environment provided by the side chains of Ser236, Glu27, and Arg320.

Indole group-containing alpha-amino amide derivatives and pharmaceutical application thereof

The invention relates to new indole group-containing alpha-amino amide derivatives represented by the structural formula I or pharmaceutically acceptable salts thereof, pharmaceutical compositions containing the compounds as active ingredients, and an application of the derivatives or the pharmaceutically acceptable salts thereof in preparation of analgesic drugs. In the structural formula I, R is a hydrogen atom or C1-C5 straight-chain alkyl or branched-chain alkyl, and the configuration of carbon atoms connected to R is an R type or an S type.

Novel alpha-amino amide derivatives and pharmaceutical use thereof

The invention relates to novel alpha-amino amide derivatives and a pharmaceutical use thereof. Specifically, the invention relates to the alpha-amino amide derivatives represented by the structural formula I or pharmaceutically acceptable salts thereof, pharmaceutical compositions containing the compounds as active ingredients, and the use of the derivatives or the pharmaceutically acceptable salts thereof for preparation of analgesic drugs.

Colorimetric and fluorescence probe for the detection of nano-molar lysine in aqueous medium

A single crystal X-ray structurally characterized BODIPY based probe, THBPY, derived from 4-hydroxy-5-isopropyl-2 methyl-isophthalaldehyde, detects nano-molar lysine in aqueous medium. In the presence of lysine, THBPY visibly changes its color and fluorescence profile due to the formation of a stable imine bond. A distinctive color change allows for facile discrimination over other amino acids in a wide range of concentrations of lysine. The detection limit for lysine is 0.001 μM by a fluorescence method and 0.01 μM by a colorimetric method. The probe shows good reversibility for multiple uses and cleanly discriminates between lysine and other amino acids. Density functional theoretical studies closely resemble experimental results.