32327-70-1Relevant articles and documents
Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
Citarella, Andrea,Holzer, Wolfgang,Ielo, Laura,Langer, Thierry,Miele, Margherita,Pace, Vittorio,Urban, Ernst,Zehl, Martin
supporting information, p. 7629 - 7634 (2020/10/12)
The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.
Ketone-catalyzed photochemical C(sp3)–H chlorination
Han, Lei,Xia, Ji-Bao,You, Lin,Chen, Chuo
, p. 3696 - 3701 (2017/06/13)
Photoexcited arylketones catalyze the direct chlorination of C(sp3)–H groups by N- chlorosuccinimide. Acetophenone is the most effective catalyst for functionalization of unactivated C–H groups while benzophenone provides better yields for benzylic C–H functionalization. Activation of both acetophenone and benzophenone can be achieved by irradiation with a household compact fluorescent lamp. This light-dependent reaction provides a better control of the reaction as compared to the traditional chlorination methods that proceed through a free radical chain propagation mechanism.
Synthetic method of 2-bromo-4-(2-chloro-ethyl)-aniline
-
Paragraph 0007, (2016/11/28)
The invention relates to a synthetic method of 2-bromo-4-(2-chloro-ethyl)-aniline and belongs to the field of chemical synthesis. The method comprises the following steps: using chlorobenzene and anhydrous AlCl2 as raw materials, dropwise adding chloroacetyl chloride, using ice water and hydrochloric acid, stirring and reacting, carrying out suction filtration, washing with sodium hydroxide and deionized water, carrying out vacuum suction filtration and collecting chlorobenzene, carrying out rotary evaporation until collecting 4-chloro-benzeneacetyl chloride, heating a 4-chloro-benzeneacetyl chloride solution, hydrazine hydrate and diglycol and carrying out reflux reaction, collecting 1-chloro-4-(2-chloroethyl)benzene and drying under reduced pressure to prepare light yellow powder, carrying out a bromination reaction and dropwise adding a sodium hypochlorite solution and an ammonium sulfite solution, washing and collecting saffron yellow particles so as to prepare 2-bromo-4-(2-chloro-ethyl)-aniline.
Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species
Nguyen, Thuy,Yang, Tianming,Go, Mei-Lin
supporting information, p. 1830 - 1838 (2015/03/14)
The in vitro neuronal cell death model based on the HT22 mouse hippocampal cell model is a convenient means of identifying compounds that protect against oxidative glutamate toxicity which plays a role in the development of certain neurodegenerative diseases. Functionalized acridin-9-yl-phenylamines were found to protect HT22 cells from glutamate challenge at submicromolar concentrations. The Aryl1-NHAryl2 scaffold that is embedded in these compounds was the minimal pharmacophore for activity. Mechanistically, protection against the endogenous oxidative stress generated by glutamate did not involve up-regulation of glutathione levels but attenuation of the late stage increases in mitochondrial ROS and intracellular calcium levels. The NH residue in the pharmacophore played a crucial role in this regard as seen from the loss of neuroprotection when it was structurally modified or replaced. That the same NH was essential for radical scavenging in cell-free and cell-based systems pointed to an antioxidant basis for the neuroprotective activities of these compounds.
Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species
Nguyen, Thuy,Yang, Tianming,Go, Mei-Lin
supporting information, p. 1830 - 1838 (2014/04/17)
The in vitro neuronal cell death model based on the HT22 mouse hippocampal cell model is a convenient means of identifying compounds that protect against oxidative glutamate toxicity which plays a role in the development of certain neurodegenerative diseases. Functionalized acridin-9-yl-phenylamines were found to protect HT22 cells from glutamate challenge at submicromolar concentrations. The Aryl1-NH-Aryl2 scaffold that is embedded in these compounds was the minimal pharmacophore for activity. Mechanistically, protection against the endogenous oxidative stress generated by glutamate did not involve up-regulation of glutathione levels but attenuation of the late stage increases in mitochondrial ROS and intracellular calcium levels. The NH residue in the pharmacophore played a crucial role in this regard as seen from the loss of neuroprotection when it was structurally modified or replaced. That the same NH was essential for radical scavenging in cell-free and cell-based systems pointed to an antioxidant basis for the neuroprotective activities of these compounds.
Gallium-catalyzed reductive chlorination of carboxylic acids with copper(II) chloride
Sakai, Norio,Nakajima, Takumi,Yoneda, Shinichiro,Konakahara, Takeo,Ogiwara, Yohei
, p. 10619 - 10623 (2015/02/19)
Described herein is the direct chlorination of carboxylic acids using copper(II) chloride via a gallium(III)-catalyzed reduction in the presence of a hydrosiloxane. During this reductive chlorination, the counteranions of CuCl2 functioned as a chloride source.
PROCESSES FOR THE PREPARATION OF 5-HT2C RECEPTOR AGONISTS
-
Page/Page column 27, (2010/12/31)
The present invention relates to processes and intermediates useful in the preparation of (R)-8-chloro-l-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (lorcaserin), a serotonin (5-ΗT) receptor modulator that is useful in the treatment of, for example, central nervous system disorders, such as obesity.
Pyrrolo[2,3-d] pyrimidines as antiviral agents
-
Scheme 2, (2010/11/29)
This invention relates to a novel class of 4,5,6,7-substituted non-nucleoside, non-phosphorylatable pyrrolo[2,3-d]pyrimidines which exhibit both significantly lower levels of cytotoxicity and superior antiviral activity than known nucleoside, non-nucleoside, and non-nucleoside, non-phosphorylatable pyrrolo[2,3-d]pyrimidine derivatives, particularly against human DNA viruses such as cytomegalovirus (HCMV) and herpes simplex virus type 1 (HSV-1). These compounds are represented by the following formula: wherein: R4is —NR1R2or oxo; R5is —CN, or —CSNR1R2, or —CONR1R2; R6is —H, or halo, or —NR1R2; wherein R1and R2are independently —H or an aliphatic group; and R7is of the formula R3—Ar, wherein R3is an aliphatic group and Ar is an unsubstituted aryl or an aryl independently substituted with halo, nitro, amino, or aliphatic groups; provided that when R5is a —CN or —CSNH2, and R6is a —H or —NH2, and Ar is a —C6H5or a phenyl substituted with only one aliphatic group, R3is an aliphatic group other than methyl such that —R3— is not a —CH2—; and pharmaceutically acceptable salts, prodrugs and derivatives thereof.
Lithiophenylalkyllithiums: New dilithium reagents having both sp2- and sp3-hybridised remote carbanionic centres
Yus, Miguel,Ramón, Diego J.,Gómez, Inmaculada
, p. 21 - 31 (2007/10/03)
The reaction of chloro-(2-chloroethyl)benzenes (1), 4-chloro-(3-chloropropyl)benzene (3) or 4-chlorophenyl chloromethyl ether (5) with lithium power using naphthalene as the electron shuttle (8 mol%) in the presence of different carbonyl compounds [Busub
1H-4(5)-substituted imidazole derivatives, their preparation and their use as histamine H3 receptor ligands
-
, (2008/06/13)
A compound of the formula wherein R2is an optionally substituted Czto Cgalkylene or alkylene chain; R3is C2to C15optionally substituted hydrocarbyl; X is a bond or —NR4—, wherein