37589-10-9Relevant academic research and scientific papers
Bisulfite Addition Compounds as Substrates for Reductive Aminations in Water
Bailey, J. Daniel,Iyer, Karthik S.,Leahy, David K.,Li, Xiaohan,Lipshutz, Bruce H.,Thakore, Ruchita R.
supporting information, p. 7205 - 7208 (2021/09/22)
Highly valued products resulting from reductive aminations utilizing shelf-stable bisulfite addition compounds of aldehydes can be made under aqueous micellar catalysis conditions. Readily available α-picolineborane serves as the stoichiometric hydride source. Recycling of the aqueous reaction medium is easily accomplished, and several applications to targets in the pharmaceutical industry are documented.
Synthesis of 3-Formylbenzenesulfonyl Chloride Derivatives
Bao, Xuefei,Liu, Ziao,Liang, Xinjie,Song, Dake,Shi, Tao,Zhao, Xuan,Bao, Changshun,Chen, Guoliang
, p. 3165 - 3170 (2017/07/12)
A synthetic route to 3-formylbenzenesulfonyl chloride derivatives from the corresponding benzaldehydes has been developed. The key step in this procedure is the conversion of aldehyde bisulfite adducts to target compounds via a two-stage reaction in the presence of Na 2 SO 4. A series of 3-formylbenzenesulfonyl chloride derivatives were prepared by this method and identified by chemical derivatization method.
Liquid-Liquid Extraction Protocol for the Removal of Aldehydes and Highly Reactive Ketones from Mixtures
Boucher, Maria M.,Furigay, Maxwell H.,Quach, Phong K.,Brindle, Cheyenne S.
, p. 1394 - 1403 (2017/09/23)
The reaction of the bisulfite ion with aldehydes to form charged bisulfite adducts is a well-established method for the purification of aldehydes. This reaction has been modified to create a convenient liquid-liquid extraction method for the removal of aldehydes from mixtures. The use of a water-miscible solvent allows the reaction to occur during a simple 30 s shaking protocol by increasing the contact between the bisulfite ion and the aldehyde. The introduction of an immiscible solvent allows for the extraction of the uncharged organic components away from the bisulfite adduct. The developed protocol is applicable to a wide range of aldehydes, including sterically hindered neopentyl aldehydes. Sterically unhindered cyclic and linear ketones, as well as highly electrophilic ketones, are also removed using this protocol. The mild conditions tolerate a wide range of functional groups, allowing for excellent aldehyde contaminant removal rates with high levels of recovery of the desired component.
Potent sirtuin inhibition with 1,2,5-trisubstituted benzimidazoles
Yoon,Osman,Choon
, p. 2094 - 2099 (2016/11/18)
Two series of compounds were synthesized based on the benzimidazole scaffold. The compounds were subsequently screened for their SIRT1, SIRT2 and SIRT3 activities. Three of the compounds showed good inhibitory activity against SIRT2 in this study with the most potent compound (5i) having an IC50 value of 2.9 μM. Molecular docking analysis demonstrated that 5i was able to inhibit SIRT2 by displacing the co-factor NAD+ in the active site. This was further confirmed experimentally by ligand-NAD+ competitive assay.
Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters
Yoon, Yeong Keng,Ali, Mohamed Ashraf,Wei, Ang Chee,Choon, Tan Soo,Ismail, Rusli
, p. 614 - 624 (2015/03/18)
Abstract A total of 51 novel benzimidazoles were synthesized by a 4-step reaction starting from basic compound 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The structure of the novel benzimidazoles was confirmed by mass spectra as well as 1H NMR spectroscopic data. Out of the 51 novel synthesized compounds, 42 of them were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv strain using BacTiter-Glo Microbial Cell Viability (BTG) method. Results of activity screened using Alamar Blue method was also provided for comparison purposes. Two of the novel benzimidazoles synthesized showed moderately good activity with IC50 of less than 15 μM. Compound 5g, ethyl 2-(4-(trifluoromethyl)phenyl)-1-(2-morpholinoethyl)-1H-benzo[d]imidazole-5-carboxylate, was found to be the most active with IC50 of 11.52 μM.
Direct reductive alkylation of amine hydrochlorides with aldehyde bisulfite adducts
Barniol-Xicota, Marta,Turcu, Andreea L.,Codony, Sandra,Escolano, Carmen,Vázquez, Santiago
supporting information, p. 2548 - 2550 (2014/05/06)
A mild procedure for the direct reaction of aromatic and aliphatic aldehyde bisulfite adducts with primary and secondary amine hydrochlorides in the presence of sodium cyanoborohydride in methanol is reported.
Synthesis and evaluation of novel benzimidazole derivatives as sirtuin inhibitors with antitumor activities
Yoon, Yeong Keng,Ali, Mohamed Ashraf,Wei, Ang Chee,Choon, Tan Soo,Osman, Hasnah,Parang, Keykavous,Shirazi, Amir Nasrolahi
, p. 703 - 710 (2014/01/23)
A total of 15 novel benzimidazole derivatives were designed, synthesized and evaluated for their SIRT1 and SIRT2 inhibitory activity. All compounds showed better inhibition on SIRT2 as compared to SIRT1. Among these, compound 5j displayed the best inhibitory activity for SIRT1 (IC50 = 58.43 μM) as well as for SIRT2 (IC50 = 45.12 μM). Cell cytotoxicity assays also showed that compound 5j possesses good antitumor activity against two different cancer cell lines derived from breast cancer (MCF-7 and MDA-MB-468). A simple structure-activity-relationship (SAR) study of the newly synthesized benzimidazole derivatives was also discussed.
Synthesis, characterization, and molecular docking analysis of novel benzimidazole derivatives as cholinesterase inhibitors
Yoon, Yeong Keng,Ali, Mohamed Ashraf,Wei, Ang Chee,Choon, Tan Soo,Khaw, Kooi-Yeong,Murugaiyah, Vikneswaran,Osman, Hasnah,Masand, Vijay H.
, p. 33 - 39 (2013/10/22)
Two series of novel acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors containing benzimidazole core structure were synthesized by a four-step reaction pathway starting from 4-fluoro-3-nitrobenzoic acid as the basic compound. The structure of the novel benzimidazoles was characterized and confirmed by the elemental and mass spectral analyses as well as 1H NMR spectroscopic data. Of the 34 novel synthesized compounds, three benzimidazoles revealed AChE inhibition with IC50 10 lM. The highest inhibitory activity (IC50 = 5.12 lM for AChE and IC50 = 8.63 lM for BChE) corresponds to the compound 5IIc (ethyl 1-(3-(1H-imidazol-1-yl)propyl)-2- (4-nitrophenyl)-1H-benzo[d]imidazole-5-carboxylate). The relationship between lipophilicity and the chemical structures as well as their limited structure-activity relationship was discussed.
A NOVEL AND VERSATILE SEPARATION METHOD FOR ALDEHYDES
Ohta, Shunsaku,Okamoto, Masao
, p. 1917 - 1919 (2007/10/02)
An aqueous solution of sodium ε-amino-n-caproate can be used for efficient and simple separation of aldehydes, overcoming the difficulties associated with the NaHSO3 method.Keywords - separation of aldehydes; Schiff base of amino acid; ω-amino acid; sodium ε-amino-n-caproate; sodium bisulfite adduct of aldehydes
