Month: October 2022

Category: bromides-buliding-blocksOn March 31, 2021, Akhtar, Muhammad Saeed; Yang, Won-Guen; Kim, Sung Hong; Lee, Yong Rok published an article in Asian Journal of Organic Chemistry. The article was 《Organic-Inorganic Dual Catalytic System for the Regioselective Construction of Diverse Quinone Derivatives via Benzannulation》. The article mentions the following:

Efficient and regioselective synthesis of highly functionalized naphthoquinones I (R1 = Me, OMe, Ph; R2 = H, Me; R3 = H, Me, Ph; R4 = H, Me, 4-methylpent-3-en-1-yl; R5 = H, Et, 3-methylbut-2-en-1-yl, n-Bu, etc.) and II (R6 = H, Me) and anthraquinone derivatives III was accomplished in good yields using an organic-inorganic dual catalyst through [4+2] cycloaddition reaction between various 1,4-benzenediols 1-4-(OH)2-2-R1-3-R2C6H2 and benzonorbornene-3,6-diol/1,4-naphthalenediol and hydroquinone and α,β-unsaturated aldehydes R4C(CH2R5)=C(R3)CHO. These atom-economic reactions rapidly provided useful cycloaddition adducts in a one-pot reaction. The technique was successfully applied to synthesize tectoquinone, a natural compound found in red heartwood-type Cryptomeria japonica, and 2-(4-methylpent-3-enyl)anthracene-9,10-dione, found in the roots of Sesamum indicum, and their analogs. After reading the article, we found that the author used 2-Bromobenzene-1,4-diol(cas: 583-69-7Category: bromides-buliding-blocks)

2-Bromobenzene-1,4-diol(cas: 583-69-7) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. Category: bromides-buliding-blocks Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Chang, Dong-Jo; Yoon, Eun-Young; Lee, Geon-Bong; Kim, Soon-Ok; Kim, Wan-Joo; Kim, Young-Myeong; Jung, Jong-Wha; An, Hongchan; Suh, Young-Ger published their research in Bioorganic & Medicinal Chemistry Letters on August 1 ,2009. The article was titled 《Design, synthesis and identification of novel colchicine-derived immunosuppressant》.Computed Properties of C9H8BrNO4 The article contains the following contents:

Colchicine-derived nitrate esters I [R = MeO, SMe, Me2N; R1 = O2NO(CH2)3, 3-(O2NOCH2)C6H4, 4-(O2NOCH2)C6H4; R2 = H, Me] and II (R3, R4, R5 = H, MeO, F, Cl, Br, I, NC, O2N, Ph) are prepared as potential immunosuppressant agents and tested for their inhibition of the allogenic mixed-lymphocyte reaction. The cytotoxicities, inhibition of NO production, and inducible nitric oxide synthase and tumor necrosis factor-α levels for I [R = MeS; R1 = O2NO(CH2)3, 3-(O2NOCH2)C6H4] are determined; the inhibition of lymphoproliferation by I [R = MeS; R1 = O2NO(CH2)3, 3-(O2NOCH2)C6H4, 4-(O2NOCH2)C6H4; R2 = H] and by II (R3 = R4 = H; R5 = F), II (R3 = Cl; R4 = R5 = H), II (R3 = R4 = H; R5 = Cl), and II (R3 = O2N; R4 = R5 = H) are also determined The cytotoxicity of II (R3 = Cl; R4 = R5 = H) and its effectiveness in increasing skin allograft survival are determined and compared to that of cyclosporin A. After reading the article, we found that the author used Methyl 5-(bromomethyl)-2-nitrobenzoate(cas: 88071-91-4Computed Properties of C9H8BrNO4)

Methyl 5-(bromomethyl)-2-nitrobenzoate(cas: 88071-91-4) 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. Computed Properties of C9H8BrNO4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Schuetz, Ramona; Mueller, Martin; Geisslinger, Franz; Vollmar, Angelika; Bartel, Karin; Bracher, Franz published their research in European Journal of Medicinal Chemistry on December 1 ,2020. The article was titled 《Synthesis, biological evaluation and toxicity of novel tetrandrine analogues》.SDS of cas: 85366-66-1 The article contains the following contents:

In this work, the design and synthesis of novel fully synthetic analogs of the bisbenzylisoquinoline tetrandrines e.g., I, a mol. with numerous pharmacol. properties and the potential to treat life-threatening diseases, such as viral infections and cancer were presented. Its toxicity to liver and lungs and the underlying mechanisms, however, are controversially discussed. Along this line, novel tetrandrine analogs e.g., I were synthesized and biol. evaluated for their hepatotoxicity, as well as their antiproliferative and chemoresistance reversing activity on cancer cells. Previous studies suggesting CYP-mediated toxification of tetrandrine prompted to amend/replace the suspected metabolically instable 12-methoxy group. Of note, employing several in vitro models showed that the proposed CYP3A4-driven metabolism of tetrandrine and analogs is not the major cause of hepatotoxicity. Biol. characterization revealed that some of the novel tetrandrine analogs e.g., I sensitized drug-resistant leukemia cells by inhibition of the P-glycoprotein. Interestingly, direct anticancer effects improved in comparison to tetrandrine, as several compounds displayed markedly enhanced ability to reduce proliferation of drug-resistant leukemia cells and to induce cell death of liver cancer cells. Those enhanced anticancer properties were linked to influences on activation of the kinase Akt and mitochondrial events. In sum, the role of CYP3A4-mediated toxicity of the bisbenzylisoquinoline alkaloid tetrandrine and the basis for exploitation of novel synthetic analogs for their antitumoral potential were clarified. The experimental process involved the reaction of 3-Bromo-4-(trifluoromethoxy)benzaldehyde(cas: 85366-66-1SDS of cas: 85366-66-1)

3-Bromo-4-(trifluoromethoxy)benzaldehyde(cas: 85366-66-1) belongs to organobromine compounds.Organobromine chemicals are produced naturally by an array of biological and other chemical processes in our environment. Some 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. SDS of cas: 85366-66-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Yuan, Zheliang; Wang, Hao-Yang; Mu, Xin; Chen, Pinhong; Guo, Yin-Long; Liu, Guosheng published an article on February 25 ,2015. The article was titled 《Highly Selective Pd-Catalyzed Intermolecular Fluorosulfonylation of Styrenes》, and you may find the article in Journal of the American Chemical Society.Reference of 4,7-Bis(4-bromophenyl)-1,10-phenanthroline The information in the text is summarized as follows:

A novel Pd-catalyzed intermol. regio- and diastereoselective fluorosulfonylation of styrenes has been developed under mild conditions. This reaction exhibits a wide range of functional-group tolerance in styrenes and arylsulfinic acids to afford various β-fluoro sulfones. Preliminary mechanistic study reveals an unusual mechanism, in which a high-valent L2PdIIIF species side-selectively reacts with a benzylic carbon radical to deliver a C-F bond. This pathway is distinct from a previously reported radical fluorination reaction. Thus, e.g., treatment of E/Z-β-methylstyrene with NFSI, p-tert-Bu-C6H4SO2H, [Pd(MeCN)4](BF4)2 and 3,4,7,8-tetramethyl-1,10-phenanthroline afforded β-fluoro sulfone I (64% from E, 73% from Z, dr > 20:1). In the experimental materials used by the author, we found 4,7-Bis(4-bromophenyl)-1,10-phenanthroline(cas: 97802-08-9Reference of 4,7-Bis(4-bromophenyl)-1,10-phenanthroline)

4,7-Bis(4-bromophenyl)-1,10-phenanthroline(cas: 97802-08-9) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals.Reference of 4,7-Bis(4-bromophenyl)-1,10-phenanthroline The most pervasive is the naturally produced bromomethane.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2012,Tamura, Yuusuke; Omori, Naoki; Kouyama, Naoki; Nishiura, Yuji; Hayashi, Kyouhei; Watanabe, Kana; Tanaka, Yukari; Chiba, Takeshi; Yukioka, Hideo; Sato, Hiroki; Okuno, Takayuki published 《Design, synthesis and identification of novel benzimidazole derivatives as highly potent NPY Y5 receptor antagonists with attractive in vitro ADME profiles》.Bioorganic & Medicinal Chemistry Letters published the findings.Name: 3-Bromo-2-methylbenzoic acid The information in the text is summarized as follows:

Optimization of the HTS hit I, mainly focused on modification at the C-2 position of the benzimidazole core, is described. Elimination of the flexible and metabolically labile -S-CH2- part and utilization of less lipophilic pyridone substructure led to identification of novel NPY Y5 receptor antagonists II (R = n-Pr, t-Bu, CF3, F3CCH2), which have low to sub-nanomolar Y5 receptor binding affinity with improved CYP450 inhibition profiles, good solubilities and high metabolic stabilities. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Name: 3-Bromo-2-methylbenzoic acid)

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. Name: 3-Bromo-2-methylbenzoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2015,Kusumi, Kensuke; Shinozaki, Koji; Kanaji, Toshiya; Kurata, Haruto; Naganawa, Atsushi; Otsuki, Kazuhiro; Matsushita, Takeshi; Sekiguchi, Tetsuya; Kakuuchi, Akito; Seko, Takuya published 《Discovery of novel S1P2 antagonists. Part 1: Discovery of 1,3-bis(aryloxy)benzene derivatives》.Bioorganic & Medicinal Chemistry Letters published the findings.Recommanded Product: 76006-33-2 The information in the text is summarized as follows:

The structure-activity relationships of a novel series of sphingosine-1-phosphate receptor antagonists have been examined in detail. The initial hit compound 1 was modified through synthesis to improve its S1P2 activity. The synthesis of a series of analogs revealed that 1,3-bis(aryloxy)benzene derivatives, as represented by 22, are potent and selective S1P2 antagonists.3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Recommanded Product: 76006-33-2) 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. Recommanded Product: 76006-33-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2016,Pitts, Cody Ross; Ling, Bill; Snyder, Joshua A.; Bragg, Arthur E.; Lectka, Thomas published 《Aminofluorination of Cyclopropanes: A Multifold Approach through a Common, Catalytically Generated Intermediate》.Journal of the American Chemical Society published the findings.Synthetic Route of C9H11Br The information in the text is summarized as follows:

We have discovered a highly regioselective aminofluorination of cyclopropanes. Remarkably, four unique sets of conditions-two photochem., two purely chem.-generated the same aminofluorinated adducts in good to excellent yields. The multiple, diverse ways in which the reaction could be initiated provided valuable clues that led to the proposal of a “”unifying”” chain propagation mechanism beyond initiation, tied by a common intermediate. In all, the proposed mechanism herein is substantiated by product distribution studies, kinetic analyses, LFERs, Rehm-Weller estimations of ΔGET, competition experiments, KIEs, fluorescence data, and DFT calculations From a more phys. standpoint, transient-absorption experiments have allowed direct spectroscopic observation of radical ion intermediates (previously only postulated or probed indirectly in photochem. fluorination systems) and, consequently, have provided kinetic support for chain propagation. Lastly, calculations suggest that solvent may play an important role in the cyclopropane ring-opening step. The results came from multiple reactions, including the reaction of 1-Bromo-2-isopropylbenzene(cas: 7073-94-1Synthetic Route of C9H11Br)

1-Bromo-2-isopropylbenzene(cas: 7073-94-1) 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.Synthetic Route of C9H11Br

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2017,Saint-Louis, Carl Jacky; Shavnore, Renee N.; McClinton, Caleb D. C.; Wilson, Julie A.; Magill, Lacey L.; Brown, Breanna M.; Lamb, Robert W.; Webster, Charles Edwin; Schrock, Alan K.; Huggins, Michael T. published 《Synthesis, computational, and spectroscopic analysis of tunable highly fluorescent BN-1,2-azaborine derivatives containing the N-BOH moiety》.Organic & Biomolecular Chemistry published the findings.Application In Synthesis of 3-Bromo-2-methylbenzoic acid The information in the text is summarized as follows:

Nine new polycyclic aromatic BN-1,2-azaborine analogs containing the N-BOH moiety were synthesized using a convenient two-step, one-pot procedure. Characterization of the prepared compounds show the luminescence wavelength and the quantum yields of the azaborines were tunable by controlling the power and location of the donor and acceptor substituents on the chromophore. UV-visible spectroscopy and d. functional theory (DFT) computations revealed that the addition of electron-donating moieties to the isoindolinone hemisphere raised the energy of the HOMO, resulting in the reduction of the HOMO-LUMO gap. The addition of an electron-accepting moiety to the isoindolinone hemisphere and an electron-donating group to the boronic acid hemisphere decreased the HOMO-LUMO gap considerably, leading to emission properties from partial intramol. charge transfer (ICT) states. The combined effect of an acceptor on the isoindolinone side and a donor on the boronic acid side (strong acceptor-π-donor) gave the most red-shifted absorption. The polycyclic aromatic BN-1,2-azaborines emitted strong fluorescence in solution and in the solid-state with the largest red-shifted emission at 640 nm and a Stokes shift of Δλ = 218 nm, or Δν = 8070 cm-1. After reading the article, we found that the author used 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Application In Synthesis of 3-Bromo-2-methylbenzoic acid)

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. Application In Synthesis of 3-Bromo-2-methylbenzoic acid The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2017,Ong, Derek Yiren; Tejo, Ciputra; Xu, Kai; Hirao, Hajime; Chiba, Shunsuke published 《Hydrodehalogenation of Haloarenes by a Sodium Hydride-Iodide Composite》.Angewandte Chemie, International Edition published the findings.Name: 1-Bromo-2-isopropylbenzene The information in the text is summarized as follows:

A simple protocol for hydrodebromination and -deiodination of halo(hetero)arenes was enabled by sodium hydride (NaH) in the presence of lithium iodide (LiI). Mechanistic studies showed that an unusual concerted nucleophilic aromatic substitution operates in the present process. After reading the article, we found that the author used 1-Bromo-2-isopropylbenzene(cas: 7073-94-1Name: 1-Bromo-2-isopropylbenzene)

1-Bromo-2-isopropylbenzene(cas: 7073-94-1) belongs to organobromine compounds. 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. Name: 1-Bromo-2-isopropylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2018,Navale, Tushar S.; Ivanov, Maxim V.; Hossain, Mohammad M.; Rathore, Rajendra published 《FHBC, a Hexa-peri-hexabenzocoronene-Fluorene Hybrid: A Platform for Highly Soluble, Easily Functionalizable HBCs with an Expanded Graphitic Core》.Angewandte Chemie, International Edition published the findings.Computed Properties of C6H5Br2N The information in the text is summarized as follows:

Materials based on hexa-peri-hexabenzocoronenes (HBCs) show significant promise in a variety of photovoltaic applications. There remains the need, however, for a soluble, versatile, HBC-based platform, which can be tailored by incorporation of electroactive groups or groups that can prompt self-assembly. The synthesis of a HBC-fluorene hybrid is presented that contains an expanded graphitic core that is highly soluble, resists aggregation, and can be readily functionalized at its vertices. This new HBC platform can be tailored to incorporate 6 electroactive groups at its vertices, as exemplified by a facile synthesis of a representative hexaaryl derivative of FHBC. Synthesis of new FHBC derivatives, containing electroactive functional groups that can allow controlled self-assembly, may serve as potential long-range charge-transfer materials for photovoltaic applications. In the experimental materials used by the author, we found 3,5-Dibromoaniline(cas: 626-40-4Computed Properties of C6H5Br2N)

3,5-Dibromoaniline(cas: 626-40-4) belongs to anime. In organic chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (NH3), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines).Computed Properties of C6H5Br2N

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary