Month: October 2022

《Discovery of Novel 3,4-Dichloroisothiazole-Containing Coumarins as Fungicidal Leads》 was written by Lv, You; Liu, Hanlu; Wang, Lifan; Li, Kun; Gao, Wei; Liu, Xiaoyu; Tang, Liangfu; Kalinina, Tatiana A.; Glukhareva, Tatiana V.; Fan, Zhijin. COA of Formula: C4H6BrFO2 And the article was included in Journal of Agricultural and Food Chemistry on April 14 ,2021. The article conveys some information:

Natural products are one of the resources for discovering novel fungicidal leads. As a natural fungicide, osthole was used as a coumarin-based lead compound for the development of novel fungicides. Here, a series of 3,4-dichloroisothiazole-containing 7-hydroxycoumarins were rationally designed, synthesized, and characterized by introducing a bioactive substructure, 3,4-dichloroisothiazole, into the coumarin skeleton. In vitro bioassay indicated that compound (I) displayed good activity against Rhizoctonia solani, Physalospora piricola, Sclerotinia sclerotiorum, and Botrytis cinerea. Its median effective concentration (EC50) value against each of these fungi fell between 0.88 and 2.50μg/mL, which was much lower than that of osthole against the corresponding pathogen (between 7.38 and 74.59μg/mL). In vivo screening validated that (II) exhibited 100%, 60%, and 20% efficacy against R. solani at 200, 100, and 50μg/mL, resp. RNA sequence anal. implied that growth inhibition of R. solani by II might result from potential disruptions of fungal membrane formation and intracellular metabolism Furthermore, a field experiment with cucumber plants indicated that (III) showed 62.73% and 74.03% efficacy against Pseudoperonospora cubensis (Berk. & Curt.) Rostov. at rates of 12.5 g a.i./ha and 25 g a.i./ha, resp., which showed no significant difference between III and osthole at 30 g a.i./ha. Our studies suggested that III, I, and II might be used as fungicidal leads for further optimization. The experimental process involved the reaction of Ethylbromofluoroacetate(cas: 401-55-8COA of Formula: C4H6BrFO2)

Ethylbromofluoroacetate(cas: 401-55-8) is a member of organofluorine compounds. Organofluorine compounds, which have carbon-fluorine bonds, show unique features such as high thermal and chemical stability, high surface activity, no light-absorbing ability, high pharmacological effect, and so on. Owing to their specific characters, they are indispensable chemicals for industry and our daily lives.COA of Formula: C4H6BrFO2

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

《Total Synthesis of Viridin and Viridiol》 was written by Ji, Yang; Xin, Zhengyuan; He, Haibing; Gao, Shuanhu. Electric Literature of C19H18BrPThis research focused onviridin viridiol total asym synthesis cycloaddition radical cyclization. The article conveys some information:

The asym. total syntheses of (-)-viridin (I) and (-)-viridiol (II), antifungal metabolites, were achieved in 17 and 18 steps, resp., from a com. available starting material. An intramol. [3+2]-cycloaddition was applied to an easily available L-ribose derivative in order to construct the highly substituted D ring containing the key chiral cis-triol fragment. Co-catalyzed metal-hydride H atom transfer (MHAT) radical cyclization was utilized to form the C-ring and the all-carbon quaternary center at C-10. This convergent strategy provides a scalable approach to prepare viridin and viridiol for biol. studies. In the experiment, the researchers used Methyltriphenylphosphonium bromide(cas: 1779-49-3Electric Literature of C19H18BrP)

Methyltriphenylphosphonium bromide(cas: 1779-49-3) is a lipophilic molecule with a cation allowing for it to be used to deliver molecules to specific cell components. Also considered an antineoplastic agent.Electric Literature of C19H18BrP

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

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

The author of 《Radical Monofluoroalkylative Alkynylation of Olefins by a Docking-Migration Strategy》 were Wang, Min; Zhang, Huihui; Liu, Jige; Wu, Xinxin; Zhu, Chen. And the article was published in Angewandte Chemie, International Edition in 2019. SDS of cas: 401-55-8 The author mentioned the following in the article:

A radical-mediated monofluoroalkylative alkynylation of alkenes is disclosed for the first time. The reaction demonstrates a remarkably broad substrate scope in which both activated and unactivated alkenes are suitable starting materials. The concurrent addition of an alkynyl and a monofluoroalkyl group onto an alkene proceeds through a docking-migration sequence, affording a vast array of valuable fluoroalkyl-substituted alkynes. Many complex natural products and drug derivatives are readily functionalized, demonstrating that this method can be used for late-stage alkynylation. In the experimental materials used by the author, we found Ethylbromofluoroacetate(cas: 401-55-8SDS of cas: 401-55-8)

Ethylbromofluoroacetate(cas: 401-55-8) is a member of organofluorine compounds. Organofluorine compounds, which have carbon-fluorine bonds, show unique features such as high thermal and chemical stability, high surface activity, no light-absorbing ability, high pharmacological effect, and so on. Owing to their specific characters, they are indispensable chemicals for industry and our daily lives.SDS of cas: 401-55-8

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

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