3679-63-8

Usage

InChI:InChI=1/C13H10ClNO2/c14-9-5-7-10(8-6-9)15-13(17)11-3-1-2-4-12(11)16/h1-8,16H,(H,15,17)

Upstream product

• 106-47-8 4-chloro-aniline 
• 69-72-7 salicylic acid 
• 1441-87-8 salicyloyl chloride 
• 104-12-1 p-chlorphenylisocyanate 
• 108-95-2 phenol 
• 90-02-8 salicylaldehyde 
• 100-00-5 4-chlorobenzonitrile 
• 110535-20-1 2-salicyloyloxy-benzoic acid-(4-chloro-anilide) 

Downstream Products

• 20978-98-7 3-(4-chloro-phenyl)-2,3-dihydro-benzo[e][1,3]oxazin-4-one 
• 18672-16-7 3-(4-chloro-phenyl)-2-methyl-2,3-dihydro-benzo[e][1,3]oxazin-4-one 
• 7133-85-9 3-(4-chlorophenyl)-2H-1,3-benzoxazine-2,4(3H)-dione 
• 955919-55-8 [2-(4-chlorophenylcarbamoyl)-phenoxy]acetic acid ethyl ester 
• 1161410-14-5 C₁₈H₁₁ClN₂O₂ 
• 1161410-06-5 C₂₀H₁₁ClN₂O₂ 
• 1206874-29-4 benzyl (S)-1-((2-(4-chlorophenylcarbamoyl)phenoxy)carbonyl)-2-methylpropylcarbamate 
• 1369423-69-7 11-(4-chlorophenyl)-3-(tetrahydro-2H-pyran-2-yl)benzo[f]pyridazino[4,5-b][1,4]oxazepine-4,10(3H,11H)-dione 
• 1321192-28-2 10-(4-chlorophenyl)-7-nitrodibenzo[b,f][1,4]oxazepin-11-(10H)-one 
• 17892-92-1 2-(4-chlorophenylcarbamoyl)phenyl acetate 
• 955919-58-1 N-(4-chlorophenyl)-2-(hydrazinocarbonylmethoxy)-benzamide 
• 955919-59-2 N-(4-chlorophenyl)-2-(1-hydrazinocarbonyl-ethoxy)-benzamide 
• 3679-64-9 bromosalicylchloranilide 
• 634584-62-6 C₄₆H₂₈Cl₂N₂O₆P₂ 

Relevant academic research and scientific papers

Synthesis and biological evaluation of JL-A7 derivatives as potent ABCB1 inhibitors

Cancer chemotherapy failure is often due to the overexpression of ATP-binding cassette (ABC) transporters (particularly ABCB1), resulting in a variety of structurally and pharmacologically unrelated drugs efflux. The multidrug resistance (MDR) phenomenon could be reversed by ABCB1 inhibitors. Now, JL-A7 as the lead compound based on a triazol-N-ethyl-tetrahydroisoquinoline scaffold, 18 compounds were designed and synthesized. Substitution in para positions yielded high activities toward ABCB1. Moreover, compound 5 could effectively block the drug efflux function of ABCB1 and increase the accumulation of anti-cancer drugs to achieve effective treatment concentration in MDR cells.

6,7-Dimethoxy-2-{2-[4-(1H-1,2,3-triazol-1-yl)phenyl]ethyl}-1,2,3,4-tetrahydroisoquinolines as superior reversal agents for P-glycoprotein-mediated multidrug resistance

P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) is a major obstacle for successful cancer chemotherapy. Based on our previous study, 17 novel compounds with the 6,7-dimethoxy-2-{2-[4-(1H-1,2,3-triazol-1-yl)phenyl]ethyl}-1,2,3,4-tetrahydroisoquinoline scaffold were designed and synthesized. Among them, 2-[(1-{4-[2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl]phenyl}-1H-1,2,3-triazol-4-yl)methoxy]-N-(p-tolyl)-benzamide (compound 7h) was identified as a potent modulator of P-gp-mediated MDR, with high potency (EC50 = 127.5 ± 9.1 nM), low cytotoxicity (TI > 784.3), and long duration (> 24 h) in reversing doxorubicin (DOX) resistance in K562/A02 cells. Compound 7h also enhanced the effects of other MDR-related cytotoxic agents (paclitaxel, vinblastine, and daunorubicin), increased the accumulation of DOX and blocked P-gp-mediated rhodamine 123 efflux function in K562/A02 MDR cells. Moreover, 7h did not have any effect on cytochrome (CYP3A4) activity. These results indicate that 7h is a relatively safe modulator of P-gp-mediated MDR that has good potential for further development.

Cooperation of a Reductant and an Oxidant in One Pot to Synthesize Amides from Nitroarenes and Aldehydes

The reductant zinc powder and the oxidant sodium chlorate were used together in an appropriate ratio in one pot under ambient conditions, to provide an environmentally friendly, effective, and convenient method for the synthesis of aromatic amides in good yields from nitroarenes and aldehydes in the green solvents alcohol and water under atmospheric conditions. The good results indicate that reductants and oxidants with opposing properties can not only be used together without any adverse effects, but also improve the reaction yield through their cooperation.

One-pot synthesis of salicylanilides by direct amide bond formation from salicyclic acid under microwave irradiation

A highly efficient protocol for the preparation of aromatic amides is described by the direct reactions between salicyclic acid and aromatic amines in the presence of phosphorous trichloride under microwave irradiation. The method has several advantages over the conventional methods, including operational simplicity, good yield, and reduced reaction time.

Synthesis and antiproliferative activities against Hep-G2 of salicylanide derivatives: Potent inhibitors of the epidermal growth factor receptor (EGFR) tyrosine kinase

A series of salicylanilide derivatives (compounds 1-32) were synthesised by reacting substituted salicylic acids and anilines. The chemical structures of these compounds were determined by 1H-NMR, electrospray ionisation mass spectrometry (ESI-MS) and elemental analysis. The compounds were assayed for their antiproliferative activities against the Hep-G2 cell line by the 3-(4,5-dimethylthylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Among the compounds tested, 22 and 28 showed the most favouable antiproliferative activities with 50% inhibitory concentration (IC50) values of 1.7 and 1.3 μM, respectively, which were comparable to the positive control of 5-fluorouracil (IC50 = 1.8 μM). A solid-phase ELISA assay was also performed to evaluate the ability of compounds 1-32 to inhibit the autophosphorylation of the epidermal growth factor receptor tyrosine kinase (EGFR TK). Docking simulations of 22 and 28 were carried out to illustrate the binding mode of the molecule into the EGFR active site, and the result suggested that both compounds 22 and 28 could bind the EGFR kinase well.

Cyclopentadienyl-free rare-earth metal amides [{(CH2SiMe 2){(2,6iPr2C6H3)N} 2}Ln{N(SiMe3)2}(THF)] as highly efficient versatile catalysts for C-C and C-N bond formation

Efficient methods have been developed for the direct synthesis of amides from aldehydes and a straightforward route to propiolamidines using cyclopentadienyl-free rare-earth metal amides [{(CH2SiMe 2){(2,6-iPr2C6H3)N} 2}Ln{N(SiMe3)2}(THF)] [Ln = Yb (1), Y (2), Dy (3), Sm (4), Nd (5)] as versatile catalysts, The results indicate that in the direct synthesis of amides from aldehydes the catalysts have the activity order 2>1～3～4～5. These methods have the advantage of easy preparation of the catalysts, low catalyst loading, high conversion of substrates to products, mild reaction conditions, and compatibility with a wide range of substrates.

Anion-triggered substituent-dependent conformational switching of salicylanilides. New hints for understanding the inhibitory mechanism of salicylanilides

(Chemical Equation Presented) A series of salicylanilides (1a-h) bearing varied substituents at the 3′- or 4′-position of the anilino moiety (substituent = p-OCH3, p-CH3, m-CH3, H, p-Cl, m-Cl, p-CO2CH3, and p-CN) were synthesized. In acetonitrile all of the substituted salicylanilides 1a-h predominantly adopt the "closed-ring" conformation facilitated by a strong intramolecular OH...O=C hydrogen bond. In the presence of H2PO4 -, the conformation of 1a-h was found to be modulated by the substituent. With our proposed proton-transfer fluorescence probing method, we were able to show that the conformation of 1a-f bearing a not highly electron-withdrawing substituent was switched to the "open-ring" form by H2PO4-, whereas 1h bearing a highly electron-withdrawing substituent, p-CN, remained in the "closed-ring" conformation. The significance of these findings for understanding, from a molecular structural point of view, the mechanism of salicylanilide-based inhibitors for inhibiting the protein tyrosine kinase epidermal growth factor receptor was discussed.

Design, synthesis, and multivariate quantitative structure-activity relationship of salicylanilides-potent inhibitors of type III secretion in Yersinia

Analogues to the salicylanilide N-(4-Chlorophenyl)-2-acetoxy-3,5- diiodobenzamide, 1a, an inhibitor of type III secretion (T3S) in Yersinia, were selected, synthesized, and biologically evaluated in three cycles. First, a set of analogues with variations in the salicylic acid ring moiety was synthesized to probe possible structural variation. A basic structure-activity relationship was established and then used to cherry-pick compounds from a principal component analysis score plot of salicylanilides to generate a second set. A third set with increased likelihood of biological activity was designed using D-optimal onion design. A quantitative structure-activity relationship model using hierarchical partial least-square regression to latent structures (Hi-PLS) was computed using PLS score vectors of building blocks correlated to the % inhibition of T3S as a response. A PLS discriminant analysis (PLS-DA) model was derived using the same descriptor set as that for the Hi-PLS model. Both models were validated with an external test set.

Process for preparing aldehyde compounds

The invention relates to a process for the making organic aldehyde compounds from an unsaturated compound by hydroformylation and in the presence of a catalyst system comprising a Group VIII metal and a bidentate phosphorus ligand having two trivalent phosphorus atoms bound to salicylanilide groups.