5409-39-2

Usage

Chemical Properties

yellow crystalline powder

InChI:InChI=1/C5H4ClN3O2/c6-3-1-4(9(10)11)5(7)8-2-3/h1-2H,(H2,7,8)/p+1

Upstream product

• 31396-27-7 5-chloro-2-nitraminopyridine 
• 1072-98-6 5-chloro-2-pyridylamine 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 71090-35-2 1,1-diamino-2-nitroethene 

Downstream Products

• 452-58-4 2,3-Diaminopyridine 
• 25710-20-7 5-chloro-2,3-diaminopyridine 
• 97941-89-4 5,6-dichloropyridine-2,3-diamine 
• 21427-62-3 2,5-dichloro-3-nitropyridine 
• 21427-61-2 5-chloro-3-nitropyridin-2-ol 
• 75806-86-9 2-bromo-5-chloro-3-nitropyridine 
• 21427-61-2 5-chloro-3-nitropyridin-2(1H)-one 
• 27330-34-3 3-amino-5-chloropicolinamide 
• 181123-11-5 5-chloro-2-cyano-3-nitropyridine 
• 27330-35-4 ethyl 3-amino-5-chloropicolinate 
• 212378-47-7 ethyl 3-phenylacetylamido-5-chloropicolinate 
• 372951-25-2 ethyl 3-(m-methyl)phenylacetylamido-5-chloropicolinate 
• 372951-22-9 ethyl 3-(p-chloro)phenylacetylamido-5-chloropicolinate 
• 372951-24-1 ethyl 3-(o-chloro)phenylacetylamido-5-chloropicolinate 

Relevant academic research and scientific papers

Convenient and practical synthesis of 6-chloro-2-(chloromethyl)- thiazolo[5,4-b]pyridine

(Chemical Equation Presented) A high-yielding and practical synthesis of 6-chloro-2-(chloromethyl)- thiazolo[5,4-b]pyridine starting from 2-amino-5-chloropyridine has been accomplished in a sequence of five steps. Copyright Taylor & Francis Group, LLC.

Design, synthesis and characterization of indole based anion sensing receptors

The design and synthesis of six new receptors (R1-R6) and their anion sensing properties through multiple channels are reported. These receptors are constructed in such a way that they possess indole groups as the binding sites and different acceptors units of varying electron acceptor strengths. Receptors R1, R3 and R5 could recognize fluoride ions visually and spectroscopically with high selectivity over other anions in DMF, which was demonstrated by a visual detection experiment and UV-Vis, fluorescence and 1H NMR spectral studies. The remaining three receptors (R2, R4 and R6) exhibited colour changes with both fluoride and cyanide ions. The binding constants for fluoride binding by these receptors were determined to be in the order of 104 to 106 M-1 and found to depend on the electron accepting property of the acceptor unit in the intra molecular charge transfer (ICT) transition existing with the indole donor units. 1H NMR titration experiments not only provide evidence for the existence of H-bonding interactions between the indolic N-H groups of these receptors and F-, but also offer key insight into the strengths of the receptor-anion complexes of stoichiometry 1:2. The higher fluoride binding ability of the receptor containing the naphthoquinone signalling unit has been interpreted in terms of the greater electron deficiency of the acceptor unit (quinone) and enhanced H-bond donating character of the indole N-H group. The results of the electrochemical and DFT computation studies corroborate well with the spectroscopic studies.

SPIRO-SUBSTITUTED OXINDOLE DERIVATIVES HAVING AMPK ACTIVITY

The present invention relates to compounds of formula (I), which have valuable pharmacological properties, in particular are activators of AMPK and which are therefore useful in the treatment of certain disorders that can be prevented or treated by activation of this receptor. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

OLEFIN SUBSTITUTED OXINDOLES HAVING AMPK ACTIVITY

The present invention relates to compounds of formula (I), which have valuable pharmacological properties, in particular are activators of AMPK and which are therefore useful in the treatment of certain disorders that can be prevented or treated by activation of this receptor. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

OXIME COMPOUNDS AND THE USE THEREOF

The invention relates to oxime compounds of Formula (I) and pharmaceutically acceptable salts, prodrugs, or solvates thereof, wherein X is hydrogen, optionally substituted aryl, optionally substituted heteroaryl or the like; Y is CO, SO2, CRsu

Clozapine derived 2,3-dihydro-1H-1,4- and 1,5-benzodiazepines with D4 receptor selectivity: Synthesis and biological testing

Novel 4-arylpiperazin-1-yl-substituted 2,3-dihydro-1H-1,4- and 1H-1,5-benzodiazepines and their aza-analogues were synthesized as debenzoclozapine derivatives for evaluation as potential D4-ligands. While Ki values of some of the title compounds came within the range of clozapine, they showed an impressively greater selectivity over other dopamine receptor subtypes, especially D2. For the most promising compounds, intrinsic activity and binding properties to serotonin 5-HT1A and 5-HT2 were also determined.

Synthesis and SAR of 5-, 6-, 7- and 8-aza analogues of 3-aryl-4-hydroxyquinolin-2(1H)-one as NMDA/glycine site antagonists

A series of 5-, 6-, 7- and 8-aza analogues of 3-aryl-4-hydroxyquinolin-2(1H)-one was synthesized and assayed as NMDA/glycine receptor antagonists. The in vitro potency of these antagonists was determined by displacement of the glycine site radioligand [3H]5,7-dicholorokynurenic acid ([3H]DCKA) in rat brain cortical membranes. Selected compounds were also tested for functional antagonism using electrophysiological assays in Xenopus oocytes expressing cloned NMDA receptor (NR) 1A/2C subunits. Among the 5-, 6-, 7-, and 8-aza-3-aryl-4-hydroxyquinoline-2(1H)-ones investigated, 5-aza-7-chloro-4-hydroxy-3-(3-phenoxyphenyl)quinolin-2-(1H)-one (13i) is the most potent antagonist, having an IC50 value of 110 nM in [3H]DCKA binding and a Kb of 11 nM in the electrophysiology assay. Compound 13i is also an active anticonvulsant when administered systemically in the mouse maximum electroshock-induced seizure test (ED50 = 2.3 mg/kg, IP).

3-[3'-hydroxymethyl)-4'-hydroxybutyl]imidazo[4,5-b]pyridines - Novel antiviral agents

Derivatives of 3- and 1-(4'-hydroxy-3'-(hydroxymethyl)butyl)-imidazo[4,5-b]pyridine were prepared in several steps from 2-amino-5-chloropyridine. Selected compounds were evaluated against human cytomegalovirus (HCMV), herpes simplex viruses (HSV1/HSV2) and varicella tester virus (VZV). Details of their synthesis and biological activities are presented.

5-(N-oxyaza)-7-substituted-1,4-dihydroquinoxaline-2,3-diones: Novel, systemically active and broad spectrum antagonists for NMDA/glycine, AMPA, and kainate receptors

A group of 5-aza-7-substituted-1,4-dihydroquinoxaline-2,3-diones (QXs) and the corresponding 5-(N. oxyaza)-7-substituted QXs were prepared and evaluated as antagonists of ionotropic glutamate receptors. The in vitro potency of these QXs was determined by inhibition of [3H]-5,7- dichlorokynurenic acid ([3H]DCKA) binding to N-methyl-D-aspartate (NMDA)/glycine receptors, [3H]-(S)-α-amino-3-hydroxy-5-methyl-4- isoxazolepropionic acid ([3H]AMPA) binding to AMPA receptors, and [3H]kainate ([3H]KA) binding to KA receptors in rat brain membranes. 5-(N- Oxyaza)-QXs 12a-e all have low micromolar or submicromolar potency for NMDA/glycine receptors and low micromolar potencies for AMPA and KA receptors. QXs 12a-e display 2-12-fold selectivity for NMDA/glycine receptors compared to AMPA receptors, and ~2-fold difference between AMPA and KA potency. In contrast to other QXs that either show high selectivity for NMDA (such as ACEA 1021) or AMPA (such as NBQX) receptors, these molecules are broad spectrum antagonists of ionotropic glutamate receptors. 7-Nitro-5-(N- axyaza)-QX (12e) is the most potent inhibitor among 12a-e, having IC50 values of 0.69, 1.3, and 2.4 μM at NMDA, AMPA, and KA receptors, respectively. In functional assays on glutamate receptors expressed in oocytes by rat cerebral cortex poly(A+) RNA, 7-chloro-5-(N-oxyaza)-QX (12a) and 7-nitro-5(N-oxyaza)-QX (12e) have K(b) values of 0.63 and 0.31 μM for NMDA/glycine receptors, and are 6- and 4-fold selective for NMDA over AMPA receptors, respectively. 5-(N-Oxyaza)-7-substituted-QXs 12a-e all have surprisingly high in vivo potency as anticonvulsants in a mouse maximal electroshock-induced seizure (MES) model. 7-Chloro-5-(N-oxyaza)-QX (12a), 7- bromo-5-(N-oxyaza)-QX (12b), and 7-methyl-5-(N-oxyaza)-QX (12c) have ED50 values of 0.82, 0.87, and 0.97 mg/kg iv, respectively. The high in vivo potency of QXs 12a-e is particularly surprising given their low log P values (~ -2.7). Separate studies indicate that QXs 12a and 12e are also active in vive as neuroprotectants and also have antinociceptive activity in animal pain models. In terms of in vivo activity, these 5-(N-oxyaza)-7-substituted- QXs are among the most potent broad spectrum ionotropic glutamate antagonists reported.