Tag: 200-300

Zhang, Hai-Lin; Yu, Ya-Ting; Wang, Yi; Tang, Qi; Yang, Shi-Ping; Liu, Jin-Gang published an article in 2021. The article was titled 《Visible light-controlled carbon monoxide delivery combined with the inhibitory activity of histone deacetylases from a manganese complex for an enhanced antitumor therapy》, and you may find the article in Journal of Inorganic Biochemistry.Synthetic Route of C5BrMnO5 The information in the text is summarized as follows:

Multifunctional drugs with synergistic effects have been widely developed to enhance the treatment efficiency of various diseases, such as malignant tumors. Herein, a novel bifunctional manganese(I)-based prodrug [MnBr(CO)3(APIPB)] (APIPB = N-(2-aminophen-yl)-4-(1H-imidazo[4,5-f] [1, 10] phenanthrolin-2-yl)benzamide) with inhibitory histone deacetylase (HDAC) activity and light-controlled carbon monoxide (CO) delivery was successfully designed and synthesized. [MnBr(CO)3(APIPB)] readily released CO under visible light irradiation (λ > 400 nm) through which the amount of released CO could be controlled by manipulating light power d. and illumination time. In the absence of light irradiation, the cytotoxic effect of [MnBr(CO)3(APIPB)] on cancer cells was greater than that of the com. available HDAC inhibitor MS-275. Consequently, with a combination of CO delivery and HDAC inhibitory activity, [MnBr(CO)3(APIPB)] showed a remarkably enhanced antitumor effect on HeLa cells (IC50 = 3.2μM) under visible light irradiation Therefore, this approach shows potential for the development of medicinal metal complexes for combined antitumor therapies. In the experimental materials used by the author, we found Bromopentacarbonylmanganese(I)(cas: 14516-54-2Synthetic Route of C5BrMnO5)

Bromopentacarbonylmanganese(I)(cas: 14516-54-2) has many other uses. It is used in the formation of (eta6-arene)tricarbonylmanganese(I) by reacting with arene (arene= hexamethyl benzene, 1,2,4,5-tetramethyl benzene, mesitylene, p-xylene and toluene) in the presence silver salt.Synthetic Route of C5BrMnO5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Grob, Nathalie M.; Schibli, Roger; Behe, Martin; Valverde, Ibai E.; Mindt, Thomas L. published an article in 2021. The article was titled 《1,5-Disubstituted 1,2,3-Triazoles as Amide Bond Isosteres Yield Novel Tumor-Targeting Minigastrin Analogs》, and you may find the article in ACS Medicinal Chemistry Letters.Application In Synthesis of Benzyl 2-bromoacetate The information in the text is summarized as follows:

1,5-Disubstituted 1,2,3-triazoles (1,5-Tz) are considered bioisosteres of cis-amide bonds. However, their use for enhancing the pharmacol. properties of peptides or proteins is not yet well established. Aiming to illustrate their utility, we chose the peptide conjugate [Nle15]MG11 (DOTA-DGlu-Ala-Tyr-Gly-Trp-Nle-Asp-Phe-NH2) as a model compound since it is known that the cholecystokinin-2 receptor (CCK2R) is able to accommodate turn conformations. Analogs of [Nle15]MG11 incorporating 1,5-Tz in the backbone were synthesized and radiolabeled with lutetium-177, and their pharmacol. properties (cell internalization, receptor binding affinity and specificity, plasma stability, and biodistribution) were evaluated and compared with [Nle15]MG11 as well as their previously reported analogs bearing 1,4-disubstituted 1,2,3-triazoles. Our investigations led to the discovery of novel triazole-modified analogs of [Nle15]MG11 with nanomolar CCK2R-binding affinity and 2-fold increased tumor uptake. This study illustrates that substitution of amides by 1,5-disubstituted 1,2,3-triazoles is an effective strategy to enhance the pharmacol. properties of biol. active peptides. In the part of experimental materials, we found many familiar compounds, such as Benzyl 2-bromoacetate(cas: 5437-45-6Application In Synthesis of Benzyl 2-bromoacetate)

Benzyl 2-bromoacetate(cas: 5437-45-6) belongs to benzyl acetate. Benzyl acetate is an aromatic chemical, usually appearing as a clear liquid with a moderate sweet-jasmine fragrance. This compound appears as a component of some of our fragrance blends.Application In Synthesis of Benzyl 2-bromoacetate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Jankowska, Agnieszka; Satala, Grzegorz; Latacz, Gniewomir; Partyka, Anna; Lubelska, Annamaria; Pociecha, Krzysztof; Swierczek, Artur; Wilczynska, Natalia; Mordyl, Barbara; Bojarski, Andrzej J.; Wyska, Elzbieta; Chlon-Rzepa, Grazyna published an article in 2021. The article was titled 《Design and Synthesis of Novel Aminoalkanamides Targeting Neurodegeneration and Symptoms of Alzheimer′s Disease》, and you may find the article in Current Medicinal Chemistry.Safety of Ethyl 5-bromovalerate The information in the text is summarized as follows:

There is currently no drug that slows the process of neurodegeneration or alleviates the cognitive and depressive symptoms in patients with Alzheimer′s disease. Due to the increasing number of Alzheimer′s patients, there is an urgent need to develop novel drugs with neuroprotective, procognitive, and antidepressant properties. The aim of this study was to design, synthesize, and evaluate novel aminoalkanamides with serotonin 5-HT1A/5-HT7 receptor affinity and phosphodiesterase (PDE) inhibitory activity as a new approach to combat neurodegeneration and symptoms of Alzheimer′s disease. The newly designed compounds were synthesized using classical methods of organic chem. and tested in vitro for their receptor affinity, functional profile, enzyme inhibition, and ADME properties. The neuroprotective effect against H2O2-induced increase of reactive oxygen species level was tested in SH-SY5Y cells. The novel object recognition and forced swimming tests were used to evaluate the procognitive and antidepressant activity, resp. Synthesized aminoalkanamides were characterized as potent 5-HT1A receptor antagonists with addnl. 5-HT7 receptor antagonistic properties and PDE4B inhibitory activity. Selected compound 15 showed neuroprotective, procognitive, and antidepressant properties. In addition, compound 15 revealed suitable ADME properties expressed as good membrane permeability and high metabolic stability. This study revealed a new class of compounds that may be useful in the search for an effective drug in the alleviation of neurodegeneration and symptoms of Alzheimer′s disease. The results came from multiple reactions, including the reaction of Ethyl 5-bromovalerate(cas: 14660-52-7Safety of Ethyl 5-bromovalerate)

Ethyl 5-bromovalerate(cas: 14660-52-7) belongs to bromides. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact.Safety of Ethyl 5-bromovalerate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2016,Mistry, Shailesh N.; Jorg, Manuela; Lim, Herman; Vinh, Natalie B.; Sexton, Patrick M.; Capuano, Ben; Christopoulos, Arthur; Lane, J. Robert; Scammells, Peter J. published 《4-Phenylpyridin-2-one Derivatives: A Novel Class of Positive Allosteric Modulator of the M1 Muscarinic Acetylcholine Receptor》.Journal of Medicinal Chemistry published the findings.Reference of Methyl 3-(bromomethyl)benzoate The information in the text is summarized as follows:

Pos. allosteric modulators (PAMs) of the M1 muscarinic acetylcholine receptor (M1 mAChR) are a promising strategy for the treatment of the cognitive deficits associated with diseases including Alzheimer’s and schizophrenia. Herein, we report the design, synthesis, and characterization of a novel family of M1 mAChR PAMs. The most active compounds of the 4-phenylpyridin-2-one series exhibited comparable binding affinity to the reference compound, 1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (BQCA), but markedly improved pos. cooperativity with acetylcholine, and retained exquisite selectivity for the M1 mAChR. Furthermore, the pharmacol. characterization revealed ligands with a diverse range of activities, including modulators that displayed both high intrinsic efficacy and PAM activity, those that showed no detectable agonism but robust PAM activity and ligands that displayed robust allosteric agonism but little modulatory activity. Compound I was found to have the best pharmacol. profile. Thus, the 4-phenylpyridin-2-one scaffold offers an attractive starting point for further lead optimization. In the experiment, the researchers used Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8Reference of Methyl 3-(bromomethyl)benzoate)

Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8) belongs to organobromine compounds.Depending on the type of carbon to which the bromine is bonded, organic bromide could be alkyl, alkenyl, alkynyl, or aryl. Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides. Reference of Methyl 3-(bromomethyl)benzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2010,Bourne, Gregory T.; Kuster, Daniel J.; Marshall, Garland R. published 《Synthesis of the Phenylpyridal Scaffold as a Helical Peptide Mimetic》.Chemistry – A European Journal published the findings.Application In Synthesis of 3-Bromo-2-methylbenzoic acid The information in the text is summarized as follows:

Phenylpyridal- and phenyldipyridal-based scaffolds have been designed and synthesized as novel helical peptide mimetics. The synthesis required optimization and selective alkylation in producing 2,6-functionalized 3-hydroxypyridine derivatives for a convergent scheme. The pyridine analogs were coupled by a series of Suzuki/Stille types cross-coupling reactions. A series of biaryl and teraryl substituted heterocycles, e.g. I, were produced. The synthetic approach was concise and high yielding allowing large variability at the wanted side-chain attachment points. A number of compounds were synthesized to show the versatility of the strategy.3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Application In Synthesis of 3-Bromo-2-methylbenzoic acid) was used in this study.

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. Application In Synthesis of 3-Bromo-2-methylbenzoic acid

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

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 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

Ren, Bo; Liu, Rong-Chun; Ji, Kegong; Tang, Jiang-Jiang; Gao, Jin-Ming published an article in Bioorganic & Medicinal Chemistry Letters. The title of the article was 《Design, synthesis and in vitro antitumor evaluation of novel pyrazole-benzimidazole derivatives》.Computed Properties of C7H5Br2F The author mentioned the following in the article:

A series of novel pyrazole-benzimidazole derivatives I [R = Br, MeO; R1 = Pr, benzyl, cinnamyl, etc.] were designed, synthesized and evaluated for their in-vitro antiproliferative activity against the HCT116, MCF-7 and Huh-7 cell lines. Among them, compounds I [R = Br, R1 = Pr, 4-(trifluoromethyl)benzyl; R = MeO, 4-cyanomethyl] showed significant antiproliferative activity against HCT116 cell lines with the IC50 values of 4.33, 5.15 and 4.84μM, resp. Moreover, fluorescent staining studies showed compound I [R = Br, R1 = 4-(trifluoromethyl)benzyl] could induce cancer cells apoptosis. The flow cytometry assay revealed that compound I [R = Br, R1 = 4-(trifluoromethyl)benzyl] could induce cell cycle arrest at G0/G1 phase. All in all, these consequences suggested that pyrazole-benzimidazole derivatives I could serve as promising compounds for further research to develop novel and highly potent cancer therapy agents. In the experiment, the researchers used 4-Bromo-1-(bromomethyl)-2-fluorobenzene(cas: 76283-09-5Computed Properties of C7H5Br2F)

4-Bromo-1-(bromomethyl)-2-fluorobenzene(cas: 76283-09-5) 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. Computed Properties of C7H5Br2F

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Formula: C11H13BrO2On May 3, 1996 ,《Synthesis and Hydrogen Bonding Capabilities of Biphenyl-Based Amino Acids Designed To Nucleate β-Sheet Structure》 appeared in Journal of Organic Chemistry. The author of the article were Nesloney, Carey L.; Kelly, Jeffery W.. The article conveys some information:

The syntheses of 3′-(aminoethyl)-2-biphenylpropionic acid (I; R = OH, R1 = H) and 2-amino-3′-biphenylcarboxylic acid (II; R = OH, R1 = H) are described. I and II were designed to nucleate β-sheet structure in aqueous solution when incorporated into small, amphiphilic peptides in place of the backbone of the i + 1 and i + 2 residues of the β-turn. Amides I and II (R = NHCH2Ph, R1 = COCH2Ph) were synthesized and studied as model compounds to investigate hydrogen-bonding capabilities. The x-ray crystal structure of I (R = NHCH2Ph, R1 = COCH2Ph) indicates that a 13-membered intramol. hydrogen-bonded ring is formed, while the remaining amide proton and carbonyl are involved in intermol. hydrogen bonding. IR and variable-temperature NMR experiments indicate that, in solution (CH2Cl2), I (R = NHCH2Ph, R1 = COCH2Ph) exists as an equilibrium mixture of the 13- and the 15-membered intramolecularly hydrogen-bonded conformers with the 15-membered ring conformer being favored. Amide II (R = NHCH2Ph, R1 = COCH2Ph) was shown to exist in solution (CH2Cl2) as an equilibrium mixture of the 11-membered intramol. hydrogen-bonded ring and a nonbonded conformation. No contribution from the 9-membered hydrogen ring conformation was observed The x-ray crystal structure of II (R = NHCH2Ph, R1 = COCH2Ph) indicated the absence of intramol. hydrogen bonding in the solid state. In the experiment, the researchers used many compounds, for example, Ethyl 3-(2-bromophenyl)propanoate(cas: 135613-33-1Formula: C11H13BrO2)

Ethyl 3-(2-bromophenyl)propanoate(cas: 135613-33-1) belongs to organobromine compounds.Organobromine chemicals are produced naturally by an array of biological and other chemical processes in our environment. Formula: C11H13BrO2Some of these compounds are identical to man-made organobromine compounds, such as methyl bromide, bromoform, and bromophenols, but many others are entirely new moleclar entities, often possessing extraordinary and important biological properties.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary