6313-54-8 Archives - Page 9 of 11 - Chlorides-buliding-blocks

Yuan, Yunyun’s team published research in Journal of Medicinal Chemistry in 55 | CAS: 6313-54-8

Journal of Medicinal Chemistry published new progress about 6313-54-8. 6313-54-8 belongs to chlorides-buliding-blocks, auxiliary class Pyridine,Chloride,Carboxylic acid, name is 2-Chloroisonicotinic acid, and the molecular formula is C12H12N2O, Computed Properties of 6313-54-8.

Yuan, Yunyun published the artcileDesign, Synthesis, and Biological Evaluation of 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4′-pyridyl)carboxamido]morphinan Derivatives as Peripheral Selective μ Opioid Receptor Agents, Computed Properties of 6313-54-8, the publication is Journal of Medicinal Chemistry (2012), 55(22), 10118-10129, database is CAplus and MEDLINE.

Peripheral selective μ opioid receptor (MOR) antagonists could alleviate the symptoms of opioid-induced constipation (OIC) without compromising the analgesic effect of opioids. However, a variety of adverse effects were associated with them, partially due to their relatively low MOR selectivity. A 6β-N-4′-pyridyl substituted naltrexamine derivative, NAP, I (R = 4-pyridyl) was identified previously as a potent and highly selective MOR antagonist mainly acting within the peripheral nervous system. The noticeable diarrhea associated with it prompted the design and synthesis of its analogs in order to study its structure-activity relationship. Among them, compound I (R = 2-methyl-4-pyridyl) showed improved pharmacol. profiles compared to the original lead, acting mainly at peripheral while increasing the intestinal motility in morphine-pelleted mice (ED₅₀ = 0.03 mg/kg). The slight decrease of the ED₅₀ compared to the original lead was well compensated by the unobserved adverse effect. Hence, this compound seems to be a more promising lead to develop novel therapeutic agents toward OIC.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Yuan, Yunyun’s team published research in Bioorganic & Medicinal Chemistry Letters in 21 | CAS: 6313-54-8

Bioorganic & Medicinal Chemistry Letters published new progress about 6313-54-8. 6313-54-8 belongs to chlorides-buliding-blocks, auxiliary class Pyridine,Chloride,Carboxylic acid, name is 2-Chloroisonicotinic acid, and the molecular formula is C22H18O2, Name: 2-Chloroisonicotinic acid.

Yuan, Yunyun published the artcileStructure selectivity relationship studies of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4′-pyridyl)carboxamido]morphinan derivatives toward the development of the mu opioid receptor antagonists, Name: 2-Chloroisonicotinic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2011), 21(18), 5625-5629, database is CAplus and MEDLINE.

Mu opioid receptor antagonists have been applied to target a variety of diseases clin. The current study is designed to explore the structure selectivity relationship (SSR) of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4′-pyridyl)carboxamido]morphinan (NAP), a lead compound identified as a selective mu opioid receptor antagonist based on the previous study. Among a series of NAP derivatives synthesized, compounds 6 (NMP) and 9 (NGP) maintained comparable binding affinity, selectivity and efficacy to the lead compound Particularly, the mu opioid receptor selectivity over kappa opioid receptor of NGP was considerably enhanced compared to that of NAP. Overall, the preliminary SSR supported our original hypothesis that an alternate address’ domain may exist in the mu opioid receptor, which favors the ligands carrying a hydrogen bond acceptor and an aromatic system to selectively recognize the mu opioid receptor.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Lindemann, Marcel’s team published research in Bioorganic & Medicinal Chemistry in 25 | CAS: 6313-54-8

Bioorganic & Medicinal Chemistry published new progress about 6313-54-8. 6313-54-8 belongs to chlorides-buliding-blocks, auxiliary class Pyridine,Chloride,Carboxylic acid, name is 2-Chloroisonicotinic acid, and the molecular formula is C6H4ClNO2, Computed Properties of 6313-54-8.

Lindemann, Marcel published the artcileDo spiroindolines have the potential to replace vesamicol as lead compound for the development of radioligands targeting the vesicular acetylcholine transporter?, Computed Properties of 6313-54-8, the publication is Bioorganic & Medicinal Chemistry (2017), 25(19), 5107-5113, database is CAplus and MEDLINE.

The vesicular acetylcholine transporter (VAChT) is an important target for in vivo imaging of neurodegenerative processes using positron emission tomog. (PET). So far the development of VAChT PET radioligands is based on the single known lead compound vesamicol. In this study we investigated a recently published spiroindoline based compound class (Sluder et al., 2012), which was suggested to have potential in the development of VAChT ligands. Therefore, we synthesized a small series of N,N-substituted spiro[indoline-3,4′-piperidine] derivatives and determined their in vitro binding affinities toward the VAChT. In order to investigate the selectivity, the off-target binding toward σ₁ and σ₂ receptors was determined The compounds possessed VAChT affinities with K_i values in the range of 39-376 nM. Binding affinities toward the σ₁ and σ₂ receptors are in a similar range indicating that the strong structural difference between the spiroindolines and vesamicol did not improve the selectivity. The observed potential to addnl. bind to σ receptors let us assume that the herein investigated spiroindolines are not suitable to replace vesamicol as lead compound for the development of VAChT ligands.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Zhang, Lei’s team published research in Bioorganic & Medicinal Chemistry Letters in 26 | CAS: 6313-54-8

Zhang, Lei published the artcileDesign, synthesis and evaluation of the multidrug resistance-reversing activity of pyridine acid esters of podophyllotoxin in human leukemia cells, Computed Properties of 6313-54-8, the publication is Bioorganic & Medicinal Chemistry Letters (2016), 26(18), 4466-4471, database is CAplus and MEDLINE.

Multidrug resistance (MDR) is the main cause for chemotherapeutic failure in cancer treatment. To overcome MDR, a series of pyridine acid esters of podophyllotoxin, I (R = 3-pyridyl, 4-chloro-2-pyridyl, 5-methoxy-2-pyridyl, etc.), was synthesized and their antiproliferation activities were evaluated against two human chronic myeloid leukemia cell lines in vitro. Most of them exhibited potent growth inhibition with IC₅₀ values in the nanomolar range as well as markedly reduced resistance factors. The most potent compound, I (R = 6-bromo-2-pyridyl) (II) exhibited an IC₅₀ of 0.046 ± 0.003 μM against resistant K562/ADR cells, showing more significant activity than that of adriamycin and etoposide, resp. Furthermore, II efficiently triggered cell cycle arrest at S phase and simultaneously induced apoptosis in K562/ADR cells. Meanwhile, II also regulated the expression levels of cell cycle- and apoptosis-related proteins. Addnl., II stimulated the ERK1/2 signaling and reduced the expression of Pgp protein. Finally, on the basis of results obtained using U0126, an ERK1/2 inhibitor, the ERK1/2 signalling pathway was proposed for the multidrug resistance-reversing effect of II in K562/ADR cells. Together, II could be a novel potential MDR reversal agent for the treatment of drug-resistant leukemia.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Liu, Jianbo’s team published research in Chem in 2021 | CAS: 6313-54-8

2-Chloroisonicotinic acid(cas: 6313-54-8) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Computed Properties of C6H4ClNO2

Liu, Jianbo; Parker, Matthew F. L.; Wang, Sinan; Flavell, Robert R.; Toste, F. Dean; Wilson, David M. published their research in Chem on August 12 ,2021. The article was titled 《Synthesis of N-trifluoromethyl amides from carboxylic acids》.Computed Properties of C6H4ClNO2 The article contains the following contents:

Here, the synthesis of N-trifluoromethyl amides R1C(O)NCF3(R2) [R1 = Et, cyclohexyl, CH2CH2Ph, etc.; R2 = Me, allyl, CH2CH2Ph, etc.] from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature was reported. Through this strategy, isothiocyanates were desulfurized with AgF, and then the formed derivative was acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method showed broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners and should find application in the modification of advanced intermediates. After reading the article, we found that the author used 2-Chloroisonicotinic acid(cas: 6313-54-8Computed Properties of C6H4ClNO2)

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Juhas, Martin’s team published research in Pharmaceuticals in 2022 | CAS: 6313-54-8

In 2022,Pharmaceuticals included an article by Juhas, Martin; Bachtikova, Andrea; Nawrot, Daria Elzbieta; Hatokova, Paulina; Pallabothula, Vinod Sukanth Kumar; Diepoltova, Adela; Jandourek, Ondrej; Barta, Pavel; Konecna, Klara; Paterova, Pavla; Sestak, Vit; Zitko, Jan. Product Details of 6313-54-8. The article was titled 《Improving Antimicrobial Activity and Physico-Chemical Properties by Isosteric Replacement of 2-Aminothiazole with 2-Aminooxazole》. The information in the text is summarized as follows:

Antimicrobial drug resistance is currently one of the most critical health issues. Pathogens resistant to last-resort antibiotics are increasing, and very few effective antibacterial agents have been introduced in recent years. The promising drug candidates are often discontinued in the primary stages of the drug discovery pipeline due to their unspecific reactivity (PAINS), toxicity, insufficient stability, or low water solubility In this work, we investigated a series of substituted N-oxazolyl- and N-thiazolylcarboxamides of various pyridinecarboxylic acids. Final compounds were tested against several microbial species. In general, oxazole-containing compounds showed high activity against mycobacteria, especially Mycobacterium tuberculosis (best MICH37Ra = 3.13 μg/mL), including the multidrug-resistant strains. Promising activities against various bacterial and fungal strains were also observed None of the compounds was significantly cytotoxic against the HepG2 cell line. Exptl. measurement of lipophilicity parameter log k′w and water solubility (log S) confirmed significantly (typically two orders in logarithmic scale) increased hydrophilicity/water solubility of oxazole derivatives in comparison with their thiazole isosteres. Mycobacterial β-ketoacyl-acyl carrier protein synthase III (FabH) was suggested as a probable target by mol. docking and mol. dynamics simulations. In the part of experimental materials, we found many familiar compounds, such as 2-Chloroisonicotinic acid(cas: 6313-54-8Product Details of 6313-54-8)

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Schwarze, Benedikt’s team published research in ChemMedChem in 2019 | CAS: 6313-54-8

In 2019,ChemMedChem included an article by Schwarze, Benedikt; Jelaca, Sanja; Welcke, Linda; Maksimovic-Ivanic, Danijela; Mijatovic, Sanja; Hey-Hawkins, Evamarie. Computed Properties of C6H4ClNO2. The article was titled 《2,2′-Bipyridine-Modified Tamoxifen: A Versatile Vector for Molybdacarboranes》. The information in the text is summarized as follows:

Investigations on the antitumor activity of metallacarboranes are sparse in the literature and limited to a handful of ruthena- and molybdacarboranes. In this study, the molybdacarborane fragment [3-(CO)2-closo-3,1,2-MoC2B9H11] was combined with a vector mol., inspired by the well-known drug tamoxifen or 4,4′-dihydroxytamoxifen (TAM-diOH). The molybdacarborane derivative [3,3-{4-[1,1-bis(4-hydroxyphenyl)but-1-en-2-yl]-2,2′-bipyridine-κ2N,N′}-3-(CO)2-closo-3,1,2-MoC2B9H11] (10), as well as the ligand itself 4-[1,1-bis(4-hydroxyphenyl)but-1-en-2-yl]-2,2′-bipyridine (6) showed cytotoxic activities in the low micromolar range against breast adenocarcinoma (MDA-MB-231, MDA-MB-361 and MCF-7), human glioblastoma (LN-229) and human glioma (U-251) cell lines. In addition, compounds 6 and 10 were found to induce senescence and cytodestructive autophagy, lower ROS/RNS levels, but only the molybdacarborane 10 induced a strong increase of nitric oxide (NO) concentration in the MCF-7 cells. In the experiment, the researchers used many compounds, for example, 2-Chloroisonicotinic acid(cas: 6313-54-8Computed Properties of C6H4ClNO2)

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Huang, Boshi’s team published research in Bioorganic Chemistry in 2021 | CAS: 6313-54-8

2-Chloroisonicotinic acid(cas: 6313-54-8) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.Safety of 2-Chloroisonicotinic acid

《Verifying the role of 3-hydroxy of 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-6β-[(4′-pyridyl)carboxamido]morphinan derivatives via their binding affinity and selectivity profiles on opioid receptors》 was written by Huang, Boshi; Gunta, Rama; Wang, Huiqun; Li, Mengchu; Cao, Danni; Mendez, Rolando E.; Gillespie, James C.; Chen, Chongguang; Huang, Lan-Hsuan M.; Liu-Chen, Lee-Yuan; Selley, Dana E.; Zhang, Yan. Safety of 2-Chloroisonicotinic acid And the article was included in Bioorganic Chemistry on April 30 ,2021. The article conveys some information:

In the present study, the role of 3-hydroxy group of a series of epoxymorphinan derivatives I (R1 = H, OH; R2 = Cl, Br, CN, Me, OMe) in their binding affinity and selectivity profiles toward the opioid receptors (ORs) has been investigated. It was found that the 3-hydroxy group was crucial for the binding affinity of these derivatives for all three ORs due to the fact that all the analogs I (R1 = OH) exhibited significantly higher binding affinities compared to their counterpart 3-dehydroxy ones I (R1 = H). Meanwhile most compounds carrying the 3-hydroxy group possessed similar selectivity profiles for the kappa opioid receptor over the mu opioid receptor as their corresponding 3-dehydroxy derivatives The [35S]-GTPγS functional assay results indicated that the 3-hydroxy group of these epoxymorphinan derivatives I was important for maintaining their potency on the ORs with various effects. Further mol. modeling studies helped comprehend the remarkably different binding affinity and functional profiles between compound I (R1 = H, R2 = CN)(NCP) and its 3-dehydroxy analog I (R1 = OH, R2 = CN). The experimental process involved the reaction of 2-Chloroisonicotinic acid(cas: 6313-54-8Safety of 2-Chloroisonicotinic acid)

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Oikonomou, Adriana’s team published research in Plant Pathology in 2022 | CAS: 6313-54-8

《Defence against Bremia lactucae conferred by the resistance gene Dm7 in lettuce is broken by treatment with dichloroisonicotinic acid》 was written by Oikonomou, Adriana; Bennett, Mark H.; Parker, Adam A. H.; Ton, Jurriaan; Mansfield, John W.. Category: chlorides-buliding-blocks And the article was included in Plant Pathology on April 30 ,2022. The article conveys some information:

The effect of inducers of systemic acquired resistance, dichloroisonicotinic acid (DCINA) and acibenzolar-S-Me (BION), on compatible interactions between Bremia lactucae and lettuce were examined using a detached cotyledon infection assay. Treatment with both activators caused a reduction in sporulation on susceptible cultivars Cobham Green challenged with isolate CL9W and Diana inoculated with isolate Tv, with DCINA being more effective than BION on an equimolar basis. Unexpectedly, treatment with both compounds suppressed the resistance conferred by the Dm7 gene in cv. Diana challenged by isolate CL9W (A7). The frequency of sporulation was greatly increased by DCINA in the incompatible interaction. The suppression of defense was associated with a delay in the onset of the Dm7-based hypersensitive reaction as indicated by the extended viability of penetrated epidermal cells, and reductions in both the accumulation of the phytoalexin lettucenin A and the deposition of autofluorescent phenolics such as syringaldehyde on plant and oomycete cell walls. The anal. of DCINA homologues indicated that 2-chloroisonicotinic acid was as effective as the dichloro-derivative in suppressing resistance in cv. Diana, whereas the absence of the carboxyl group rendered 2,6-dichloropyridine inactive. Infection of cotyledons by Botrytis cinerea was also found to be enhanced by DCINA treatment. Based on our results, we discuss the possibility that DCINA reduces Dm7 transcription through an epigenetic mechanism, as is supported by bioinformatic analyses of the resistance gene, and that it suppresses jasmonate-dependent resistance to B. cinerea. The results came from multiple reactions, including the reaction of 2-Chloroisonicotinic acid(cas: 6313-54-8Category: chlorides-buliding-blocks)

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Zhao, Xiaoqing’s team published research in Inorganica Chimica Acta in 2020 | CAS: 6313-54-8

COA of Formula: C6H4ClNO2On May 1, 2020 ,《A series of luminescent LnIII-based coordination polymers: Syntheses, structures and luminescent properties》 appeared in Inorganica Chimica Acta. The author of the article were Zhao, Xiaoqing; Zhang, Fenhang; Liu, Yajun; Zhao, Tianhao; Zhao, Hongyan; Xiang, Shuo; Li, Yunchun. The article conveys some information:

A series of lanthanide coordination polymers (Ln-CPs), with the formula of {[Ln(L)3(CH3OH)(H2O)]n} (Ln = Sm (1), Eu (2), HL = 2-chloroisonicotinic acid) and {[Ln(L)3(H2O)2]n} (Ln = Dy (3), Tb (4)), were synthesized under solvothermal condition. This series display two different 1D chains due to the lanthanide contraction: complexes 1 and 2, based on light Sm and Eu, resp., consist of paddle-wheel [Ln2(COO)4] dimmers through double μ2-COO bridges, and complexes 3 and 4 with heavy Dy and Tb, resp., show 1D [Ln(COO)2]n chains. The luminescent measurements indicate the typical emissions of corresponding Ln3+ ions in complexes 1-4. Furthermore, complexes 2 and 4 display significant luminescent response for Fe3+ ions with high quenching constant Complexes 2 and 4 can act as luminescent probes for Fe3+ ions with relatively high sensitivity and selectivity. In the experimental materials used by the author, we found 2-Chloroisonicotinic acid(cas: 6313-54-8COA of Formula: C6H4ClNO2)

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics