Category: 76006-33-2

In 2014,Carbain, Benoit; Paterson, David J.; Anscombe, Elizabeth; Campbell, Allyson J.; Cano, Celine; Echalier, Aude; Endicott, Jane A.; Golding, Bernard T.; Haggerty, Karen; Hardcastle, Ian R.; Jewsbury, Philip J.; Newell, David R.; Noble, Martin E. M.; Roche, Celine; Wang, Lan Z.; Griffin, Roger J. published 《8-Substituted O6-Cyclohexylmethylguanine CDK2 Inhibitors: Using Structure-Based Inhibitor Design to Optimize an Alternative Binding Mode》.Journal of Medicinal Chemistry published the findings.HPLC of Formula: 76006-33-2 The information in the text is summarized as follows:

Evaluation of the effects of purine C-8 substitution within a series of CDK1/2-selective O6-cyclohexylmethylguanine derivatives revealed that potency decreases initially with increasing size of the alkyl substituent. Structural anal. showed that C-8 substitution is poorly tolerated, and to avoid unacceptable steric interactions, these compounds adopt novel binding modes. Thus, 2-amino-6-cyclohexylmethoxy-8-isopropyl-9H-purine adopts a “”reverse”” binding mode where the purine backbone has flipped 180°. This provided a novel lead chemotype from which we have designed more potent CDK2 inhibitors using, in the first instance, quantum mech. energy calculations Introduction of an ortho-tolyl or ortho-chlorophenyl group at the purine C-8 position restored the potency of these “”reverse”” binding mode inhibitors to that of the parent 2-amino-6-cyclohexylmethoxy-9H-purine. By contrast, the corresponding 8-(2-methyl-3-sulfamoylphenyl)-purine derivative exhibited submicromolar CDK2-inhibitory activity by virtue of engineered addnl. interactions with Asp86 and Lys89 in the reversed binding mode, as confirmed by X-ray crystallog. In addition to this study using 3-Bromo-2-methylbenzoic acid, there are many other studies that have used 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2HPLC of Formula: 76006-33-2) was used in this study.

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. HPLC of Formula: 76006-33-2 The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

OuYang, Yiqiang; Gao, Jian; Zhao, Lei; Lu, Junfeng; Zhong, Haiqing; Tang, Hua; Jin, Shuanglong; Yue, Lu; Li, Yuezhen; Guo, Wenjie; Xu, Qiang; Lai, Yisheng published their research in Journal of Medicinal Chemistry in 2021. The article was titled 《Design, Synthesis, and Evaluation of o-(Biphenyl-3-ylmethoxy)nitrophenyl Derivatives as PD-1/PD-L1 Inhibitors with Potent Anticancer Efficacy In Vivo》.Product Details of 76006-33-2 The article contains the following contents:

Two series of novel o-(biphenyl-3-ylmethoxy)nitrophenyl compounds I (R1 = 2-hydroxyethylamino, furan-ylmethylamino, (2-acetamidoethyl)aminyl, etc.; R2 = H, Me, Br) and II (R3 = 3-cyanobenzyloxy, 3-pyridinylmethoxy, 2-cyanopyridin-4-ylmethoxy) were designed as programmed cell death protein 1 (PD-1)/PD-ligand 1 (PD-L1) inhibitors. All compounds showed significant inhibitory activity with IC50 values ranging from 2.7 to 87.4 nM except compound I (R1 = (2S)-2-aminyl-3-hydroxybutanoic acid), and compound II (III, R1 = (2S)-2-aminyl-3-hydroxybutanoic acid; R3 = 3-cyanobenzyloxy) displayed the best activity. Further experiments showed that III bound to the PD-L1 protein without obvious toxicity in Lewis lung carcinoma (LLC) cells. Furthermore, III significantly promoted interferon-gamma secretion in a dose-dependent manner in vitro and in vivo. Especially, III exhibited potent in vivo anticancer efficacy in an LLC-bearing allograft mouse model at a low dose of 5 mg/kg, which was more active than BMS-1018 (tumor growth inhibition rate: 48.5% vs 17.8%). A panel of immunohistochem. and flow cytometry assays demonstrated that III effectively counteracted PD-1-induced immunosuppression in the tumor microenvironment, thereby triggering antitumor immunity. These results indicate that III is a promising PD-1/PD-L1 inhibitor worthy of further development. After reading the article, we found that the author used 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Product Details of 76006-33-2)

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) belongs to organobromine compounds.Organobromine chemicals are produced naturally by an array of biological and other chemical processes in our environment. Organobromine compounds are produced naturally by marine creatures (sponges, corals, sea slugs, tunicates, sea fans) and seaweed, plants, fungi, lichen, algae, bacteria, microbes, and some mammals. Product Details of 76006-33-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Xu, Xi; Zhang, Di; Zhao, Tengteng; Wang, Min; Li, Yu; Du, Qianming; Kou, Junping; Li, Zhiyu; Bian, Jinlei published an article in 2022. The article was titled 《Novel biphenyl-based scaffold as potent and selective histone deacetylase 6 (HDAC6) inhibitors: Identification, development and pharmacological evaluation》, and you may find the article in European Journal of Medicinal Chemistry.Related Products of 76006-33-2 The information in the text is summarized as follows:

A series of novel biphenyl-based scaffold derivatives were identified as selective histone deacetylase 6 (HDAC6) inhibitors through an inhouse compound library screening approach. The biol. evaluation indicated that most of target compounds exhibited moderate to good inhibitory activity and selectivity against HDAC6. Especially, compound C10 was identified as a potent and highly selective HDACs inhibitor, with HDAC1 IC50 value of 3600 nM, HDAC6 IC50 value of 23 nM, and the HDAC1/6 selectivity index of 157. Moreover, C10 displayed robust anti-proliferative activity, induced cancer cells apoptosis, increased the level of acetylated α-tubulin and inhibited cancer cells migration in vitro. C10 showed significant antitumor efficacy (TGI: 75%) in CT26 colon carcinoma xenograft model in mice with no considerable toxicity in vivo. More importantly, C10 could also activate antitumor immunity so as to synergistically exert antitumor effects in vivo. Overall, our findings have provided a new avenue for design, development and investigation into the mechanism underlying the antitumor efficacy of selective HDAC6 inhibitors. The experimental part of the paper was very detailed, including the reaction process of 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Related Products of 76006-33-2)

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) belongs to organobromine compounds.Most of the natural organobromine compounds are produced by marine organisms , and several brominated metabolites with antibacterial , antitumor , antiviral , and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. Related Products of 76006-33-2 Moreover, several studies demonstrate that the average proportion of bromine in drugs is significantly higher than that in natural products.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 1993,Stoilov, Ivan; Watt, David S.; Goodman, Jack P.; St. Pyrek, Jan published 《Synthesis of detomidine and medetomidine metabolites: 1,2,3-trisubstituted arenes with 4′(5′)-imidazolylmethyl groups》.Journal of Heterocyclic Chemistry published the findings.Electric Literature of C8H7BrO2 The information in the text is summarized as follows:

Two synthetic strategies permitted the synthesis of various metabolites of detomidine (I, R = H, X = Me) and medetomidine I (R = X = Me), potent α-2 adrenoceptor agonists that undergo rapid oxidative metabolism at the aromatic Me group distal to the imidazole ring. In the detomidine series, the addition of a Grignard reagent prepared from 2-[(3′,4′-dimethoxyphenyl)methoxy]methyl-6-bromotoluene to imidazole-4(5)-carboxyaldehyde provided 2-(((3′,4′-dimethoxyphenyl)methoxy)methyl)-6-(1′-hydroxy-1′-(5”-imidazolyl)methyl)toluene. In a subsequent reduction, it was possible to differentiate between the secondary benzylic hydroxyl group and the primary benzylic hydroxyl group protected as a 3,4-dimethoxybenzyl ether. Removal of the protecting group provided 3-(hydroxymethyl)detomidine (3-HD) I (R = H, X = CH2OH) and an oxidation furnished 3-carboxydetomidine (3-CD) I (R = H, X = CO2H). However, in the medetomidine series, a similar hydrogenolysis of 2-(((3′,4′-dimethoxyphenyl)methoxy)methyl)-6-(1′-hydroxy-1′-(5”-imidazolyl)methyl)toluene failed, and an alternate, longer route involving dehydration and reduction was necessary to secure 3-(hydroxymethyl)medetomidine (3-HM) I (R = Me, X = CH2OH) and following an oxidation, 3-carboxymedetomidine (3-CM) I (R = Me, X = CO2H). Finally, an expeditious route to 3-CM involved the addition of the Grignard reagent prepared from 2-(3-bromo-2-methylphenyl)-4,4-dimethyl-2-oxazoline to 4-acetyl-1H-imidazole and the hydrogenolysis and hydrolysis of 2-(1-(4,4-dimethyl-2-oxazolyl))-6-(1′-oxo-1′-(5′-imidazolyl)methyl)toluene. The experimental process involved the reaction of 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Electric Literature of C8H7BrO2)

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Electric Literature of C8H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2011,Chandrakantha, B.; Isloor, Arun M.; Philip, Reji; Mohesh, M.; Shetty, Prakash; Vijesh, A. M. published 《Synthesis and nonlinear optical characterization of new 1,3,4-oxadiazoles》.Bulletin of Materials Science published the findings.Formula: C8H7BrO2 The information in the text is summarized as follows:

1,3,4-Oxadiazole derivatives containing 2-fluoro-4-methoxy Ph were synthesized by refluxing mixture of acid hydrazide with different aromatic carboxylic acids in phosphorous oxychloride. These newly synthesized compounds were characterized by NMR, mass spectral, and IR spectral studies, and also by C, H, N analyses. The open-aperture z-scan experiment was employed to measure the optical nonlinearity of the samples at 532 nm, using 5 ns laser pulses. The measurements indicate that one of the compounds which contains Br, behaves as an optical limiter at this wavelength, with potential applications in optoelectronics. The experimental part of the paper was very detailed, including the reaction process of 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Formula: C8H7BrO2)

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals.Formula: C8H7BrO2 The most pervasive is the naturally produced bromomethane.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

COA of Formula: C8H7BrO2In 2017 ,《Small-Molecule Inhibitors of the Programmed Cell Death-1/Programmed Death-Ligand 1 (PD-1/PD-L1) Interaction via Transiently Induced Protein States and Dimerization of PD-L1》 appeared in Journal of Medicinal Chemistry. The author of the article were Guzik, Katarzyna; Zak, Krzysztof M.; Grudnik, Przemyslaw; Magiera, Katarzyna; Musielak, Bogdan; Torner, Ricarda; Skalniak, Lukasz; Domling, Alexander; Dubin, Grzegorz; Holak, Tad A.. The article conveys some information:

Blockade of the PD-1/PD-L1 immune checkpoint pathway with monoclonal antibodies has provided significant advances in cancer treatment. The antibody-based immunotherapies carry a number of disadvantages such as the high cost of the antibodies, their limited half-life, and immunogenicity. Development of small-mol. PD-1/PD-L1 inhibitors that could overcome these drawbacks is slow because of the incomplete structural information for this pathway. The first chem. PD-1/PD-L1 inhibitors have been recently disclosed by Bristol-Myers Squibb. Here we present NMR and X-ray characterization for the two classes of these inhibitors. The X-ray structures of the PD-L1/inhibitor complexes reveal one inhibitor mol. located at the center of the PD-L1 homodimer, filling a deep hydrophobic channel-like pocket between two PD-L1 mols. Derivatives of (2-methyl-3-biphenylyl)methanol exhibit the structures capped on one side of the channel, whereas the compounds based on [3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methanol induce an enlarged interaction interface that results in the open “”face-back”” tunnel through the PD-L1 dimer. In the experiment, the researchers used 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2COA of Formula: C8H7BrO2)

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) belongs to organobromine compounds.Most of the natural organobromine compounds are produced by marine organisms , and several brominated metabolites with antibacterial , antitumor , antiviral , and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. Moreover, several studies demonstrate that the average proportion of bromine in drugs is significantly higher than that in natural products. COA of Formula: C8H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Nonpeptide Urotensin-II Receptor Antagonists: A New Ligand Class Based on Piperazino-Phthalimide and Piperazino-Isoindolinone Subunits》 was written by Lawson, Edward C.; Luci, Diane K.; Ghosh, Shyamali; Kinney, William A.; Reynolds, Charles H.; Qi, Jenson; Smith, Charles E.; Wang, Yuanping; Minor, Lisa K.; Haertlein, Barbara J.; Parry, Tom J.; Damiano, Bruce P.; Maryanoff, Bruce E.. Safety of 3-Bromo-2-methylbenzoic acidThis research focused onurotensin receptor antagonist preparation structure activity piperazino phthalimide isoindolinone. The article conveys some information:

We have discovered two related chem. series of nonpeptide urotensin-II (U-II) receptor antagonists based on piperazino-phthalimide (5 and 6) and piperazino-isoindolinone (7) scaffolds. These structure types are distinctive from those of U-II receptor antagonist series reported in the literature. One of the antagonists exhibited single-digit nanomolar potency in rat and human cell-based functional assays, as well as strong binding to the human U-II receptor. In advanced pharmacol. testing, one of the antagonists blocked the effects of U-II in vitro in a rat aortic ring assay and in vivo in a rat ear-flush model. A discussion of U-II receptor antagonist pharmacophores is presented, and a specifically defined model is suggested from tricycle compound, which has a high degree of conformational constraint. In the part of experimental materials, we found many familiar compounds, such as 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Safety of 3-Bromo-2-methylbenzoic acid)

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals.Safety of 3-Bromo-2-methylbenzoic acid Organobromine compounds have fallen under increased scrutiny for their environmental impact.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 1980,Yagoub, Ahmed K.; Iskander, George M. published 《Evidence for the mechanism of formation of N-(1,2-dihydrobenzocyclobut-1-enyl)pyridinium bromides and acetophenones from bisdibromocyclopropane adducts》.Journal of the Chemical Society published the findings.Synthetic Route of C8H7BrO2 The information in the text is summarized as follows:

Bis(dibromocarbene) adducts I (R = H, R1 = OMe, OEt; R = Me, R1 = OMe) on heating with xylene and 1,4-diazabicyclo[2.2.2]octane gave the corresponding bicyclooctadienes II, which gave pyridinium salts III with pyridine). In contrast, reaction of pyridine with I (R = Me; R1 = OMe, OEt) and with bicyclic ketone IV gave phenylacylpyridinium salt V. The preparation of 4,2,3-MeO(Br)2C6H2COMe from I (R = H, R1 = OMe) is also reported. In addition to this study using 3-Bromo-2-methylbenzoic acid, there are many other studies that have used 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Synthetic Route of C8H7BrO2) was used in this study.

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) belongs to organobromine compounds.Most of the natural organobromine compounds are produced by marine organisms , and several brominated metabolites with antibacterial , antitumor , antiviral , and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. Synthetic Route of C8H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2009,Katritzky, Alan R.; Tala, Srinivasa R.; Lu, Hong; Vakulenko, Anatoliy V.; Chen, Qi-Yin; Sivapackiam, Jothilingam; Pandya, Keyur; Jiang, Shibo; Debnath, Asim K. published 《Design, Synthesis, and Structure-Activity Relationship of a Novel Series of 2-Aryl 5-(4-Oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans as HIV-1 Entry Inhibitors》.Journal of Medicinal Chemistry published the findings.Product Details of 76006-33-2 The information in the text is summarized as follows:

We previously identified two small mols. targeting the HIV-1 gp41, N-(4-carboxy-3-hydroxy)phenyl-2,5-dimethylpyrrole (I) and N-(3-carboxy-4-chloro)phenylpyrrole (II), that inhibit HIV-1 infection at low micromolar levels. On the basis of mol. docking anal., we designed a series of 2-aryl 5-(4-oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans, e.g. III. Compared with I and II, these compounds have bigger mol. size (437-515 Da) and could occupy more space in the deep hydrophobic pocket on the gp41 NHR trimer. Fifteen 2-aryl 5-(4-oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans were synthesized by Suzuki-Miyaura cross-coupling followed by a Knoevenagel condensation and tested for their anti-HIV-1 activity and cytotoxicity on MT-2 cells. We found that all 15 compounds had improved anti-HIV-1 activity and 3 of them exhibited inhibitory activity against replication of HIV-1IIIB and 94UG103 at <100 nM range, more than 20-fold more potent than I and II, suggesting that these compounds can serve as leads for development of novel small mol. HIV fusion inhibitors. The experimental process involved the reaction of 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Product Details of 76006-33-2)

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals.Product Details of 76006-33-2 Organobromine compounds have fallen under increased scrutiny for their environmental impact.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2010,Kasuga, Jun-ichi; Ishikawa, Minoru; Yonehara, Mitsuhiro; Makishima, Makoto; Hashimoto, Yuichi; Miyachi, Hiroyuki published 《Improvement of water-solubility of biarylcarboxylic acid peroxisome proliferator-activated receptor (PPAR) δ-selective partial agonists by disruption of molecular planarity/symmetry》.Bioorganic & Medicinal Chemistry published the findings.Reference of 3-Bromo-2-methylbenzoic acid The information in the text is summarized as follows:

To elucidate the mol. basis of peroxisome proliferator-activated receptor (PPAR) δ partial agonism, X-ray crystal structures of complexes of the PPARδ ligand-binding site with partial agonists are required. Unfortunately, reported PPARδ partial agonists, biphenylcarboxylic acids 1 and 2, possess insufficient aqueous solubility to allow such crystals to be obtained. To improve the aqueous solubility of 1 and 2, substituents were introduced at the 2-position of the biaryl moiety, focusing on disruption of mol. planarity and symmetry. All 2-substituted biphenyl analogs examined showed more potent PPARδ agonistic activity with greater aqueous solubility than 1 or 2. Among these biphenyls, 25 showed potent and selective PPARδ partial agonistic activity (EC50: 5.7 nM), with adequate solubility in phosphate buffer (0.022 mg/mL). The 2-substituted pyridyl analog 27 showed weaker PPARδ partial agonistic activity (EC50: 76 nM) with excellent solubility in phosphate buffer (2.7 mg/mL; at least 2700 times more soluble than 2). Our results indicate that two strategies to improve aqueous solubility, i.e., introduction of substituent(s) to modify the dihedral angle and to disrupt mol. symmetry, may be generally applicable to bicyclic mols. Combination of these approaches with the traditional approach of reducing the mol. hydrophobicity may be particularly effective. After reading the article, we found that the author used 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Reference of 3-Bromo-2-methylbenzoic acid)

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) belongs to organobromine compounds.Organobromine chemicals are produced naturally by an array of biological and other chemical processes in our environment. Organobromine compounds are produced naturally by marine creatures (sponges, corals, sea slugs, tunicates, sea fans) and seaweed, plants, fungi, lichen, algae, bacteria, microbes, and some mammals. Reference of 3-Bromo-2-methylbenzoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary