Month: January 2023

Discovery of N-(3,4-Dimethylphenyl)-4-(4-isobutyrylphenyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline-8-sulfonamide as a Potent Dual MDM2/XIAP Inhibitor was written by Wu, Zhongzhi;Gu, Lubing;Zhang, Sicheng;Liu, Tao;Lukka, Pradeep B.;Meibohm, Bernd;Bollinger, John C.;Zhou, Muxiang;Li, Wei. And the article was included in Journal of Medicinal Chemistry in 2021.Formula: C6H5Br2N This article mentions the following:

Murine double minute 2 (MDM2) and X-linked inhibitor of apoptosis protein (XIAP) are important cell survival proteins in tumor cells. As a dual MDM2/XIAP inhibitor reported previously, compound MX69 has low potency with an IC₅₀ value of 7.5μM against an acute lymphoblastic leukemia cell line EU-1. Herein, we report the structural optimization based on the MX69 scaffold, leading to the discovery of a 25-fold more potent analog 14 (IC₅₀ = 0.3μM against EU-1). We demonstrate that 14 maintains its mode of action by dual targeting of MDM2 and XIAP through inducing MDM2 protein degradation and inhibiting XIAP mRNA translation, resp., which resulted in cancer cell growth inhibition and cell death. The results strongly suggest that the scaffold based on 14 is promising for further optimization to develop a new therapeutic agent for leukemia and possibly other cancers where MDM2 and XIAP are dysregulated. In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Formula: C6H5Br2N).

3,4-Dibromoaniline (cas: 615-55-4) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Formula: C6H5Br2N

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

7′-Substituted Benzothiazolothio- and Pyridinothiazolothio-Purines as Potent Heat Shock Protein 90 Inhibitors was written by Zhang, Lin;Fan, Junhua;Vu, Khang;Hong, Kevin;Le Brazidec, Jean-Yves;Shi, Jiandong;Biamonte, Marco;Busch, David J.;Lough, Rachel E.;Grecko, Roy;Ran, Yingqing;Sensintaffar, John L.;Kamal, Adeela;Lundgren, Karen;Burrows, Francis J.;Mansfield, Robert;Timony, Gregg A.;Ulm, Edgar H.;Kasibhatla, Srinivas R.;Boehm, Marcus F.. And the article was included in Journal of Medicinal Chemistry in 2006.SDS of cas: 615-55-4 This article mentions the following:

We report on the discovery of benzo- and pyridino- thiazolothiopurines as potent heat shock protein 90 inhibitors. The benzothiazole moiety is exceptionally sensitive to substitutions on the aromatic ring with a 7′-substituent essential for activity. Some of these compounds exhibit low nanomolar inhibition activity in a Her-2 degradation assay (28-150 nM), good aqueous solubility, and oral bioavailability profiles in mice. In vivo efficacy experiments demonstrate that compounds of this class inhibit tumor growth in an N87 human colon cancer xenograft model via oral administration as shown with compound 37 (8-(7-chlorobenzothiazol-2-ylsulfanyl)-9-(2-cyclopropylamino-ethyl)-9H- purin-6-ylamine)(I). In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4SDS of cas: 615-55-4).

3,4-Dibromoaniline (cas: 615-55-4) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.SDS of cas: 615-55-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Practical synthesis of some novel unsymmetrical 1,3-dialkylpyrimidine derivatives at room temperature was written by Khalafi-Nezhad, Ali;Zare, Abdolkarim;Parhami, Abolfath;Rad, Mohammad N. Soltani. And the article was included in ARKIVOC (Gainesville, FL, United States) in 2006.Quality Control of N-(5-Bromopentyl)phthalimide This article mentions the following:

The efficient synthesis of some novel unsym. 1,3-dialkylpyrimidines is described. N(3)-Alkylation of N(1)-substituted pyrimidine derivatives with various functionalized alkyl halides in the presence of catalytic amounts of tetrabutylammonium bromide (TBAB) and Cs₂CO₃ in MeCN affords the title compounds The reactions proceed at room temperature, and the products are obtained in good to excellent yields. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Quality Control of N-(5-Bromopentyl)phthalimide).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Quality Control of N-(5-Bromopentyl)phthalimide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design, synthesis of some novel thiazolidin-4-one derivatives bearing benzimidazole nucleus and biological evaluation of their possible in vitro antiinflammatory as cyclooxygenase inhibitors and antioxidant activity was written by Sahoo, U.;Seth, A. K.;Balaraman, R.;Velmurugan, R.. And the article was included in Asian Journal of Chemistry in 2015.Application of 85118-24-7 This article mentions the following:

A series of 2-[2-(4-cyanophenyl)-6-substituted-1H-benzimidazol-1-yl]-N-[2-(substituted)-4-oxo-1,3- thiazolidin-3-yl]acetamide I (R¹ = Cl, NO₂; R² = 4-H₃COC₆H₄, 3-BrC₆H₄, 1H-pyrazol-3-ylphenyl, etc.) were synthesized. The substituted o-phenylenediamines were reacted with substituted 4-cyanobenzaldehydes in the presence of sodium metabisulfite to furnish substituted 2-(4-cyanophenyl)-1H-benzimidazoles II. The N-alkylated product (2-(4-cyanophenyl)-benzimidazol-1-yl)-acetic acid Et esters were obtained by the further treatment of substituted 2-(4-cyanophenyl)-1H-benzimidazoles with Et chloroacetate in KOH/DMSO. The chem. reactions were conducted between hydrazine hydrate and the esters to synthesize 2-(4-cyanophenyl)-benzimidazol-1-yl-acetic acid hydrazides. When a mixture of 2-(4-cyanophenyl)-benzimidazol-1-yl-acetic acid hydrazides reacted with substituted aldehydes in ethanol, imine intermediates were formed. The reactions between a mixture of imine intermediates and thioglycollic acid in dioxane resulted in the formation of the title compound I. All the synthesized compounds were screened for their in vitro antioxidant and antiinflammatory activity. The in vitro antioxidant and antiinflammatory activity might be attributed due to the presence of more electrons withdrawing group and moiety having more lipophilicity also more electronegativity in nature. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Application of 85118-24-7).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Application of 85118-24-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Derivatized cyclodextrins as peptidomimetics: influence on neurite growth was written by Borrajo, Alison M. P.;Gorin, Boris I.;Dostaler, Suzanne M.;Riopelle, Richard J.;Thatcher, Gregory R. J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 1997.Formula: C42H63Br7O28 This article mentions the following:

Per-6-bromo-6-deoxy-cyclodextrins may be functionalized to yield amine-derivatized cyclodextrin mimics of glycosaminoglycan sulfate binding domains of peptides, which inhibit neurite growth in vitro. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Formula: C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Formula: C42H63Br7O28

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Regio- and Enantioselective Ni-Catalyzed Formal Hydroalkylation, Hydrobenzylation, and Hydropropargylation of Acrylamides to α-Tertiary Amides was written by Shi, Lou;Xing, Ling-Ling;Hu, Wen-Bo;Shu, Wei. And the article was included in Angewandte Chemie, International Edition in 2021.Category: bromides-buliding-blocks This article mentions the following:

The development of enantioselective alkyl-alkyl cross-couplings with coinstantaneous formation of a stereogenic center without the use of sensitive organometallic species is attractive yet challenging. Herein, we report the intermol. regio- and enantioselective formal hydrofunctionalizations of acrylamides, forging a stereogenic center α-position to the newly formed C_sp3-C_sp3 bond for the first time. The use of a newly developed chiral ligand enables the electronically-reversed formal hydrofunctionalizations, including hydroalkylation, hydrobenzylation, and hydropropargylation, offering an efficient way to access diverse enantioenriched amides with a tertiary α-stereogenic carbon center which is facile to racemize. This operationally simple protocol allows for the anti-Markovnikov enantioselective hydroalkylation, and unprecedented hydrobenzylation, hydropropargylation under mild conditions with excellent functional group compatibility, delivering a wide range of amides with excellent levels of enantioselectivity. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Category: bromides-buliding-blocks).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Rh(III)-Catalyzed One-Step Synthesis of ortho-Alkynylated Perylene Imide Dyes: Optical and Electrochemical Properties of New Derivatives was written by Chand, Tapasi;Khamari, Laxmikanta;Chopra, Deepak;Mukherjee, Saptarshi;Kapur, Manmohan. And the article was included in Chemistry – A European Journal in 2022.Name: 1-Bromopyrrolidine-2,5-dione This article mentions the following:

A one-step Rh-catalyzed site-selective ortho-C-H alkynylation of perylene as well as naphthalene mono- and diimides is reported. A single step regioselective access to ortho-C-H alkynylated derivatives of these aryleneimides not only increases the step economy of the ortho-functionalization on these dyes but also provides a quick access route toward highly functionalized dyes that have potential optoelectronic applications. Increased solubility of tetra(triisopropylsilyl)acetylenyl PDIs in organic solvents greatly enhances their utility for further derivatization. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Name: 1-Bromopyrrolidine-2,5-dione).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Name: 1-Bromopyrrolidine-2,5-dione

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Metal-Free TEMPO-Promoted C(sp³)-H Amination To Afford Multisubstituted Benzimidazoles was written by Xue, Ding;Long, Ya-Qiu. And the article was included in Journal of Organic Chemistry in 2014.Name: 2-(Bromomethyl)-1,3-dimethylbenzene This article mentions the following:

An efficient TEMPO-air/cat.TEMPO-O₂ oxidative protocol was developed to synthesize multisubstituted or fused tetracyclic benzimidazoles via a metal-free oxidative C-N coupling between the sp³ C-H and free N-H of readily available N¹-benzyl/alkyl-1,2-phenylenediamines. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7Name: 2-(Bromomethyl)-1,3-dimethylbenzene).

2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Name: 2-(Bromomethyl)-1,3-dimethylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Three-Component Olefin Dicarbofunctionalization Enabled by Nickel/Photoredox Dual Catalysis was written by Campbell, Mark W.;Compton, Jordan S.;Kelly, Christopher B.;Molander, Gary A.. And the article was included in Journal of the American Chemical Society in 2019.Recommanded Product: Ethyl 4-bromo-2-fluorobenzoate This article mentions the following:

An intermol., photocatalytic dicarbofunctionalization (DCF) of olefins enabled by the merger of Giese-type addition with Ni/photoredox dual catalysis was realized. Capitalizing on the rapid addition of 3° radicals to alkenes and their reluctance toward single electron metalation to Ni complexes, regioselective alkylation and arylation of olefins is possible. This dual catalytic method not only permits elaborate species to be assembled from commodity materials, but also allows quaternary and tertiary centers to be installed in a singular, chemoselective olefin difunctionalization. This multicomponent process occurs under exceptionally mild conditions, compatible with a diverse range of functional groups and synthetic handles such as pinacolboronate esters. This technol. was directly applied to the synthesis of an intermediate to a preclin. candidate (TK-666) and its derivatives In the experiment, the researchers used many compounds, for example, Ethyl 4-bromo-2-fluorobenzoate (cas: 474709-71-2Recommanded Product: Ethyl 4-bromo-2-fluorobenzoate).

Ethyl 4-bromo-2-fluorobenzoate (cas: 474709-71-2) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Recommanded Product: Ethyl 4-bromo-2-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Robust Maleimide-Functionalized Gold Surfaces and Nanoparticles Generated Using Custom-Designed Bidentate Adsorbates was written by Park, Chul Soon;Lee, Han Ju;Jamison, Andrew C.;Lee, T. Randall. And the article was included in Langmuir in 2016.Formula: C15H29BrO2 This article mentions the following:

A series of custom-designed alkanethioacetate ligands were synthesized to provide a facile method of attaching maleimide-terminated adsorbates to gold nanostructures via thiolate bonds. Monolayers on flat gold substrates derived from both mono- and dithioacetates, with and without oligo(ethylene glycol) (OEG) moieties in their alkyl spacers, were characterized using XPS, polarization modulation IR reflection-absorption spectroscopy, ellipsometry, and contact angle goniometry. For all adsorbates, the resulting monolayers revealed that a higher packing d. and more homogeneous surface were generated when the film was formed in EtOH, but a higher percentage of bound thiolate was obtained in THF. A series of gold nanoparticles (AuNPs) capped with each adsorbate were prepared to explore how adsorbate structure influences aqueous colloidal stability under extreme conditions, as examined visually and spectroscopically. The AuNPs coated with adsorbates that include OEG moieties exhibited enhanced stability under high salt concentration, and AuNPs capped with dithioacetate adsorbates exhibited improved stability against ligand exchange in competition with dithiothreitol (DTT). Overall, the best results were obtained with a chelating dithioacetate adsorbate that included OEG moieties in its alkyl spacer, imparting improved stability via enhanced solubility in water and superior adsorbate attachment owing to the chelate effect. In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Formula: C15H29BrO2).

15-Bromopentadecanoic acid (cas: 56523-59-2) 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. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Formula: C15H29BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary