Category: 33697-81-3

Cho, Yongsung published the artcileThe SAR analysis of TRPV1 agonists with the α-methylated B-region, Name: 3-Chloro-4-hydroxyphenylacetic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2012), 22(16), 5227-5231, database is CAplus and MEDLINE.

A series of TRPV1 agonists with amide, reverse amide, and thiourea groups in the B-region and their corresponding α-methylated analogs were investigated. Whereas the α-methylation of the amide B-region enhanced the binding affinities and potencies as agonists, that of the reverse amide and thiourea led to a reduction in receptor affinity. The anal. indicated that proper hydrogen bonding as well as steric effects in the B-region are critical for receptor binding.

Bioorganic & Medicinal Chemistry Letters published new progress about 33697-81-3. 33697-81-3 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Phenol, name is 3-Chloro-4-hydroxyphenylacetic acid, and the molecular formula is C8H7ClO3, Name: 3-Chloro-4-hydroxyphenylacetic acid.

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

Sato, Masakazu published the artcileSynthesis and evaluation of novel thiazolidine derivatives as thromboxane A₂ receptor antagonists, Related Products of chlorides-buliding-blocks, the publication is Chemical & Pharmaceutical Bulletin (1994), 42(3), 521-9, database is CAplus and MEDLINE.

3-Benzoyl or 3-phenylsulfonyl-2-substituted thiazolidine derivatives were prepared, and evaluated for their thromboxane A₂ (TXA₂) receptor-antagonizing effect on (15S)-15-hydroxy-11α,9α-(epoxymethano)prostathiazolidine derivative, 3-benzoyl-2-(4-hydroxy-3-methoxyphenyl)thiazolidine, showed mild TXA₂ receptor antagonist activity. Modification of the compound led to 2-chloro-4-[3-(4-chlorophenylsulfonyl)thiazolidin-2-ylmethyl]phenoxyacetates I (X = H, Cl; R² = H, OMe, halo; n = 0-2), one of which showed TXA₂ receptor antagonist activity.

Chemical & Pharmaceutical Bulletin published new progress about 33697-81-3. 33697-81-3 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Phenol, name is 3-Chloro-4-hydroxyphenylacetic acid, and the molecular formula is C8H7ClO3, Related Products of chlorides-buliding-blocks.

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

Kormos, Chad M. published the artcileDiscovery of N-{4-[(3-Hydroxyphenyl)-3-methylpiperazin-1-yl]methyl-2-methylpropyl}-4-phenoxybenzamide Analogues as Selective Kappa Opioid Receptor Antagonists, Computed Properties of 33697-81-3, the publication is Journal of Medicinal Chemistry (2013), 56(11), 4551-4567, database is CAplus and MEDLINE.

There is continuing interest in the discovery and development of new κ opioid receptor antagonists. We recently reported that N-substituted 3-methyl-4-(3-hydroxyphenyl)piperazines were a new class of opioid receptor antagonists. In this study, we report the syntheses of two piperazine JDTic-like analogs. Evaluation of the two compounds in an in vitro [³⁵S]GTPγS binding assay showed that neither compound showed the high potency and κ opioid receptor selectivity of JDTic. A library of compounds was synthesized by amidation of compound I with com. available arylcarboxylic acids and tested for their ability to inhibit [³⁵S]GTPγS binding stimulated by the selective κ opioid agonist U69,593. These studies led to N-[(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyl}-2-methylpropyl]-4-phenoxybenzamide (II), a compound that showed good κ opioid receptor antagonist properties. An SAR study based on II provided 28 novel analogs. Evaluation of these 28 compounds in the [³⁵S]GTPγS binding assay showed that several of the analogs were potent and selective κ opioid receptor antagonists.

Journal of Medicinal Chemistry published new progress about 33697-81-3. 33697-81-3 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Phenol, name is 3-Chloro-4-hydroxyphenylacetic acid, and the molecular formula is C8H7ClO3, Computed Properties of 33697-81-3.

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

Xu, Weifeng published the artcileAbscisic acid accumulation modulates auxin transport in the root tip to enhance proton secretion for maintaining root growth under moderate water stress, Related Products of chlorides-buliding-blocks, the publication is New Phytologist (2013), 197(1), 139-150, database is CAplus and MEDLINE.

Summary : Maintenance of root growth is essential for plant adaptation to soil drying. Here, we tested the hypothesis that auxin transport is involved in mediating ABA’s modulation by activating proton secretion in the root tip to maintain root growth under moderate water stress. Rice and Arabidopsis plants were raised under a hydroponic system and subjected to moderate water stress (-0.47 MPa) with polyethylene glycol (PEG). ABA accumulation, auxin transport and plasma membrane H+-ATPase activity at the root tip were monitored in addition to the primary root elongation and root hair d. We found that moderate water stress increases ABA accumulation and auxin transport in the root apex. Addnl., ABA modulation is involved in the regulation of auxin transport in the root tip. The transported auxin activates the plasma membrane H+-ATPase to release more protons along the root tip in its adaptation to moderate water stress. The proton secretion in the root tip is essential in maintaining or promoting primary root elongation and root hair development under moderate water stress. These results suggest that ABA accumulation modulates auxin transport in the root tip, which enhances proton secretion for maintaining root growth under moderate water stress.

New Phytologist published new progress about 33697-81-3. 33697-81-3 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Phenol, name is 3-Chloro-4-hydroxyphenylacetic acid, and the molecular formula is C14H10O4, Related Products of chlorides-buliding-blocks.

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

Reemtsma, T. published the artcilePotential of ethyl acetate in the determination of extractable organic halogens (EOX) from contaminated soil, sediment, and sewage sludge, Formula: C8H7ClO3, the publication is Chemosphere (1996), 32(5), 815-26, database is CAplus.

The potential of Me tert-Bu ether, toluene and Et acetate for determining extractable organic halogens (EOX) from contaminated soil, lake sediments and sewage sludge was studied and compared with hexane, which is prescribed in the German standard method of EOX determination Soxhlet-extraction with Et acetate proved most efficient and yielded 2-6 times the EOX-values obtained by hexane. Washing of Et acetate extracts is not necessary, since interferences by coextd. inorganic halides was negligible if dried samples are extracted The detection limit is at 0.1-0.2 μg g^-1 with standard deviations between 3-7%. The method was further evaluated by application onto soil samples spiked with 3-chloro-4-hydroxy-phenylacetic acid (I) and phosphoric acid-tris-(2-chloroethyl) ester (II). Et acetate recoveries were 45-52% for I and 77-110% for II, compared with 6-13% recovery by hexane. Et acetate extraction substantially improves the EOX-determination but it might still underestimate the true value. For all sewage sludge, soil and sediment samples the EOX/EOM (extractable organic matter) ratio did also increase using Et acetate. This indicates the importance of polar halogenated contaminants which are amenable by Et acetate extraction rather than by hexane. The implications of EOX/EOM ratios for EOX dynamics are discussed.

Chemosphere published new progress about 33697-81-3. 33697-81-3 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Phenol, name is 3-Chloro-4-hydroxyphenylacetic acid, and the molecular formula is C8H7ClO3, Formula: C8H7ClO3.

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

Ngoma Tchibouanga, Remi Rolland published the artcile3-Chloro-4-hydroxyphenylacetic acid co-crystals with nicotinamide, isonicotinamide, phenazine and 4,4′-bipyridine: An investigation of synthon motifs, Recommanded Product: 3-Chloro-4-hydroxyphenylacetic acid, the publication is Journal of Molecular Structure (2020), 127195, database is CAplus.

Multicomponent crystals of 3-chloro-4-hydroxyphenylacetic acid (CHPAA) with nicotinamide (NAM), isonicotinamide (INAM), phenazine (PHZN) and 4,4′-bipyridine (BIPY) were successfully synthesized by the slow evaporation technique. The co-crystals were characterized using x-ray diffraction, thermal anal., FTIR spectroscopy and Hirshfeld surface anal. Both NAM and INAM co-crystal structures exhibited O-H···N and N-H···O interactions. The INAM co-crystal structure demonstrated the tetrameric amide homosynthon. The incorporation of H₂O into the NAM co-crystal structure resulted in addnl. O-H···O H bonds. PHZ and BIPY co-crystal structures displayed O-H···N interactions. The 2CHPAA•BIPY structure also showed an interesting CHPAA dimer with a head to tail motif characterized by O-H···O and formed a H bonded ring described as R²₂(18). Weaker interactions C-H···O, C-H···Cl and π ··· π stacking were also observed in the crystal structures. Alternate preparation methods such as grinding and slurry experiments were also explored. Crystallog. data are given.

Journal of Molecular Structure published new progress about 33697-81-3. 33697-81-3 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Phenol, name is 3-Chloro-4-hydroxyphenylacetic acid, and the molecular formula is C8H7ClO3, Recommanded Product: 3-Chloro-4-hydroxyphenylacetic acid.

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

Van de Pas, Bram A. published the artcileEnergy yield of respiration on chloroaromatic compounds in Desulfitobacterium dehalogenans, Category: chlorides-buliding-blocks, the publication is Applied and Environmental Microbiology (2001), 67(9), 3958-3963, database is CAplus and MEDLINE.

The amount of energy that can be conserved via halorespiration by Desulfitobacterium dehalogenans JW/IU-DC1 was determined by comparison of the growth yields of cells grown with 3-chloro-4-hydroxyphenyl acetate (Cl-OHPA) and different electron donors. Cultures that were grown with lactate, pyruvate, formate, or hydrogen as an electron donor and Cl-OHPA as an electron acceptor yielded 3.1, 6.6, 1.6, and 1.6 g (dry weight) per mol of reduction equivalent, resp. Fermentative growth on pyruvate yielded 14 g (dry weight) per mol of pyruvate oxidized. Pyruvate was not fermented stoichiometrically to acetate and lactate, but an excess of acetate was produced. Experiments with ¹³C-labeled bicarbonate showed that during pyruvate fermentation, approx. 9% of the acetate was formed from the reduction of CO₂. Comparison of the growth yields suggests that 1 mol of ATP is produced per mol of acetate produced by substrate-level phosphorylation and that there is no contribution of electron transport phosphorylation when D. dehalogenans grows on lactate plus Cl-OHPA or pyruvate plus Cl-OHPA. Furthermore, the growth yields indicate that approx. 1/3 mol of ATP is conserved per mol of Cl-OHPA reduced in cultures grown in formate plus Cl-OHPA and hydrogen plus Cl-OHPA. Because neither formate nor hydrogen nor Cl-OHPA supports substrate-level phosphorylation, energy must be conserved through the establishment of a protonmotive force. Pyruvate ferredoxin oxidoreductase, lactate dehydrogenase, formate dehydrogenase, and hydrogenase were localized by in vitro assays with membrane-impermeable electron acceptors and donors. The orientation of chlorophenol-reductive dehalogenase in the cytoplasmic membrane, however, could not be determined A model is proposed, which may explain the topol. analyses as well as the results obtained in the yield study.

Applied and Environmental Microbiology published new progress about 33697-81-3. 33697-81-3 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Phenol, name is 3-Chloro-4-hydroxyphenylacetic acid, and the molecular formula is C4H6BrFO2, Category: chlorides-buliding-blocks.

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

Mani, Ali R. published the artcileThe Metabolism and Dechlorination of Chlorotyrosine in Vivo, Related Products of chlorides-buliding-blocks, the publication is Journal of Biological Chemistry (2007), 282(40), 29114-29121, database is CAplus and MEDLINE.

During inflammation, neutrophil- and monocyte-derived myeloperoxidase catalyzes the formation of hypochlorous acid, which can chlorinate tyrosine residues in proteins to form chlorotyrosine. However, little is known of the metabolism and disposition of chlorotyrosine in vivo. Following infusion of deuterium-labeled [D₄]chlorotyrosine into Sprague-Dawley rats, the major urinary metabolites were identified by mass spectrometry. 3-Chloro-4-hydroxyphenylacetic acid was identified as the major chlorinated metabolite of chlorotyrosine and accounted for 3.6 ± 0.3% of infused [D₄]chlorotyrosine. The striking observation was that ∼40% (39 ± 1%) of infused [D₄]chlorotyrosine was dechlorinated and excreted in the urine as deuterated 4-hydroxyphenylacetic acid, a major metabolite of tyrosine. 1.1 ± 0.1% of infused [D₄]chlorotyrosine was excreted as [D₄]tyrosine. To determine whether protein-bound chlorotyrosine could undergo dechlorination, chlorinated albumin was incubated with liver homogenate from mutant rats, which did not synthesize albumin. There was ∼20% decrease in the chlorotyrosine content over 1 h. This study is the first to describe the dechlorination of chlorotyrosine as the major metabolic pathway to eliminate this modified amino acid in vivo.

Journal of Biological Chemistry published new progress about 33697-81-3. 33697-81-3 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Phenol, name is 3-Chloro-4-hydroxyphenylacetic acid, and the molecular formula is C8H7ClO3, Related Products of chlorides-buliding-blocks.

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

Davis, Rohan A. published the artcileCarbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library, Recommanded Product: 3-Chloro-4-hydroxyphenylacetic acid, the publication is Bioorganic & Medicinal Chemistry (2010), 18(1), 14-18, database is CAplus and MEDLINE.

We have investigated the enzyme inhibition characteristics of a natural product (NP)-based phenolic library against a panel of human carbonic anhydrases (hCAs, EC 4.2.1.1) which included hCAs I and II (cytosolic) and hCA VA/VB (mitochondrial isoforms). Most of these compounds were weak, micromolar inhibitors of the two cytosolic hCAs (K _Is >10 μM) but showed good hCA VA/VB inhibitory activity with inhibition constants in the range of 70-125 nM. The selectivity ratios for inhibiting the mitochondrial over the cytosolic isoforms for these phenol derivatives were in the range of 120-3800, making them the most isoform-selective compounds for inhibiting hCA VA/VB known to date. The CA VA/VB enzymes are involved in biosynthetic processes such as gluconeogenesis, lipogenesis and ureagenesis, and no pharmacol. inhibitors with good selectivity are currently available. Thus the NP inhibitors identified during these studies are excellent leads for obtaining even more effective compounds that selectively target mitochondrial hCAs, and also have the potential to be used as tools for understanding the physiol. processes that are regulated by the two mitochondrial CA isoforms.

Bioorganic & Medicinal Chemistry published new progress about 33697-81-3. 33697-81-3 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Phenol, name is 3-Chloro-4-hydroxyphenylacetic acid, and the molecular formula is C8H7ClO3, Recommanded Product: 3-Chloro-4-hydroxyphenylacetic acid.

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

Hoyerova, Klara published the artcileAuxin molecular field maps define AUX1 selectivity: many auxin herbicides are not substrates, Application of 3-Chloro-4-hydroxyphenylacetic acid, the publication is New Phytologist (2018), 217(4), 1625-1639, database is CAplus and MEDLINE.

Summary : Developmental responses to auxin are regulated by facilitated uptake and efflux, but detailed mol. understanding of the carrier proteins is incomplete. We have used pharmacol. tools to explore the chem. space that defines substrate preferences for the auxin uptake carrier AUX1. Total and partial loss-of-function aux1 mutants were assessed against wild-type for dose-dependent resistance to a range of auxins and analogs. We then developed an auxin accumulation assay with associated math. modeling to enumerate accurate IC50 values for a small library of auxin analogs. The structure activity relationship data were analyzed using mol. field analyses to create a pharmacophoric atlas of AUX1 substrates. The uptake carrier exhibits a very high level of selectivity towards small substrates including the natural indole-3-acetic acid, and the synthetic auxin 2,4-dichlorophenoxyacetic acid. No AUX1 activity was observed for herbicides based on benzoic acid (dicamba), pyridinyloxyacetic acid (triclopyr) or the 6-arylpicolinates (halauxifen), and very low affinity was found for picolinic acid-based auxins (picloram) and quinolinecarboxylic acids (quinclorac). The atlas demonstrates why some widely used auxin herbicides are not, or are very poor substrates. We list mol. descriptors for AUX1 substrates and discuss our findings in terms of herbicide resistance management.

New Phytologist published new progress about 33697-81-3. 33697-81-3 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Phenol, name is 3-Chloro-4-hydroxyphenylacetic acid, and the molecular formula is C8H7ClO3, Application of 3-Chloro-4-hydroxyphenylacetic acid.

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