Month: February 2023

Fluoroaryl analogs of sulforaphane – A group of compounds of anticancer and antimicrobial activity was written by Cierpial, Tomasz;Kielbasinski, Piotr;Kwiatkowska, Malgorzata;Lyzwa, Piotr;Lubelska, Katarzyna;Kuran, Dominika;Dabrowska, Aleksandra;Kruszewska, Hanna;Mielczarek, Lidia;Chilmonczyk, Zdzislaw;Wiktorska, Katarzyna. And the article was included in Bioorganic Chemistry in 2020.Formula: C13H14BrNO2 This article mentions the following:

A series of new sulforaphane analogs bearing various (poly)fluoroaryl substituents bonded to the sulfinyl sulfur atom in place of the original Me group and having different number of methylene groups in the central alkyl chain were synthesized and fully characterized. The new compounds were tested in vitro for their anticancer, antibacterial, antifungal and antiviral properties. Some of them demonstrated a much higher anticancer activity against selected lines of cancer: skin (MALME-3M), colon (HT-29) and breast (MCF7 and MDA-MB-231) cells than that exhibited by native sulforaphane (SFN). Related lines of untransformed (normal) cells, taken from the same organs as the cancer ones, i.e. MALME3, CRL-1790 and MCF10, resp., were checked, which allowed for the determination of the selectivity indexes (SI). In certain cases, the latter exceeded 3.2. Concerning the antibacterial activity, gram-pos. bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) were susceptible to some newly synthesized SFN analogs, while the selected probiotic strains were from 10 to 100 fold more resistant to them, which gives a possibility of protection of symbiont strains during a potential therapy with such compounds The antifungal activity of the new compounds possessing the fluorophenyl substituent was found to be higher than the activity of the parent SFN. In turn, most of the new compounds showed generally no anti-HIV activity. The influence of the particular structural differences in the new mols., analogs of SFN, on their biol. activity is discussed. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Formula: C13H14BrNO2).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) 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: C13H14BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Hypervalent Chalcogenonium…π Bonding Catalysis was written by Zhang, Qingyu;Chan, Yung-Yin;Zhang, Muyin;Yeung, Ying-Yeung;Ke, Zhihai. And the article was included in Angewandte Chemie, International Edition in 2022.SDS of cas: 128-08-5 This article mentions the following:

A proof-of-concept study of hypervalent chalcogenonium…π bonding catalysis was performed. A new catalytic strategy using 1,2-oxaselenolium salts as chalcogen bond donors and alkenes as chalcogen bond acceptors is described. The feasibility of this concept is demonstrated by the use of trisubstituted selenonium salts in the metal-free catalytic hydrofunctionalization and polymerization of alkenes via unconventional seleniranium ion-like intermediates. The results indicate that counter anions have a significant effect on the catalysis based on hypervalent chalcogenonium…π bonding interactions. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5SDS of cas: 128-08-5).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.SDS of cas: 128-08-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Structure-Based Drug Design of Bisubstrate Inhibitors of Phenylethanolamine N-Methyltransferase Possessing Low Nanomolar Affinity at Both Substrate Binding Domains¹ was written by Lu, Jian;Bart, Aaron G.;Wu, Qian;Criscione, Kevin R.;McLeish, Michael J.;Scott, Emily E.;Grunewald, Gary L.. And the article was included in Journal of Medicinal Chemistry in 2020.Reference of 954-81-4 This article mentions the following:

The enzyme phenylethanolamine N-methyltransferase (PNMT, EC 2.1.1.28) catalyzes the final step in the biosynthesis of epinephrine and is a potential drug target, primarily for the control of hypertension. Unfortunately, many potent PNMT inhibitors also possess significant affinity for the a₂-adrenoceptor, which complicates the interpretation of their pharmacol. A bisubstrate analog approach offers the potential for development of highly selective inhibitors of PNMT. This paper documents the design, synthesis, and evaluation of such analogs, several of which were found to possess human PNMT (hPNMT) inhibitory potency <5 nM vs. AdoMet. Site-directed mutagenesis studies were consistent with bisubstrate binding. Two of these compounds (19 and 29) were co-crystallized with hPNMT and the resulting structures revealed both compounds bound as predicted, simultaneously occupying both substrate binding domains. This bisubstrate inhibitor approach has resulted in one of the most potent (20) and selective (vs the a_2-adrenoceptor) inhibitors of hPNMT yet reported. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Reference of 954-81-4).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) 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). 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.Reference of 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Pyrrole as a Directing Group: Regioselective Pd(II)-Catalyzed Alkylation and Benzylation at the Benzene Core of 2-Phenylpyrroles was written by Wahl, Johannes M.;Poethig, Alexander;Bach, Thorsten. And the article was included in Organic Letters in 2016.Reference of 954-81-4 This article mentions the following:

Pyrrole has been employed for the first time as a directing group in the Pd(II)-catalyzed ortho-functionalization of C(sp²)-H bonds. A variety of substituted 2-phenylpyrroles were successfully methylated, alkylated, or benzylated in the ortho-position of the benzene ring, yielding the resp. 2-substituted pyrrol-2-yl benzenes (36 examples, 51-93% yield). Neither additives nor addnl. ligands were required to perform the reaction, which was routinely conducted with PdBr₂ as the catalyst and Li₂CO₃ as the base. Mechanistically, there is evidence that precoordination of palladium to the pyrrole enables the regioselective ortho-attack. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Reference of 954-81-4).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) 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 principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Reference of 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Non-ionic thiolated cyclodextrins – the next generation was written by Moghadam, Ali;Ijaz, Muhammad;Asim, Mulazim Hussain;Mahmood, Arshad;Jelkmann, Max;Matuszczak, Barbara;Bernkop-Schnuerch, Andreas. And the article was included in International Journal of Nanomedicine in 2018.Synthetic Route of C42H63Br7O28 This article mentions the following:

The current study was aimed at developing a novel mucoadhesive thiolated cyclodextrin (CD) without ionizable groups and an intact ring backbone for drug delivery. Thiolated beta CD (β-CD) was prepared through bromine substitution of its hydroxyl groups followed by replacement to thiol groups using thiourea. The thiolated β-CD was characterized in vitro via dissolution studies, cytotoxicity studies, mucoadhesion studies on freshly excised porcine intestinal mucosa, and inclusion complex formation with miconazole nitrate. Thiolated β-CDs namely β-CD-SH₆₀₀ and β-CD-SH₁₂₀₀ displayed 558.66 ± 78 and 1,163.45 ± 96 μmol thiol groups per g of polymer, resp. Stability constant (Kc) of 190 M^-1 confirmed the inclusion complex formation of miconazole nitrate with β-CD-SH. Inclusion complexes of β-CD-SH₆₀₀ and β-CD-SH₁₂₀₀ resulted in 157- and 257-fold increased solubility of miconazole nitrate, resp. In addition, more than 80% of thiol groups were stable even after 6 h at pH 5. Both β-CD-SH compounds showed at least 1.3-fold improved solubility in water. In contrast to cationic thiolated CDs of the first generation, both thiomers showed no significant cytotoxicity. The mucoadhesive properties of the new thiolated CDs were 39.73- and 46.37-fold improved, resp. These results indicate that β-CD-SH might provide a new favorable tool for delivery of poorly soluble drugs providing a prolonged residence time on mucosal surfaces. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Synthetic Route of C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) 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.Synthetic Route of C42H63Br7O28

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Palladium-catalyzed diastereoselective cross-coupling of two aryl halides via C-H activation: synthesis of chiral eight-membered nitrogen heterocycles was written by Cheng, Cang;Zuo, Xiang;Tu, Dongdong;Wan, Bin;Zhang, Yanghui. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.SDS of cas: 173026-23-8 This article mentions the following:

A method for the synthesis of enantiopure eight-membered nitrogen heterocycles, e.g., I was developed through diastereoselective cross-coupling of 2-iodobiphenyls with 2-bromobenzylamines. The products represented a novel type of chiral scaffold, which feature easy modification and high configurative stability and had the potential to be applied in asym. synthesis. Palladacycles that were formed via the C-H activation of 2-iodobiphenyls should act as the intermediates. The reaction provided a new strategy for the synthesis of medium-sized ring compounds In the experiment, the researchers used many compounds, for example, 2-(2-Bromophenyl)propan-2-amine (cas: 173026-23-8SDS of cas: 173026-23-8).

2-(2-Bromophenyl)propan-2-amine (cas: 173026-23-8) 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. 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: 173026-23-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Halogenated Bis(methoxybenzylidene)-4-piperidone Curcuminoids with Improved Anticancer Activity was written by Schmitt, Florian;Subramaniam, Dharmalingam;Anant, Shrikant;Padhye, Subhash;Begemann, Gerrit;Schobert, Rainer;Biersack, Bernhard. And the article was included in ChemMedChem in 2018.Formula: C8H6Br2O2 This article mentions the following:

A series of readily available curcuminoids with a halogenated bis(4-methoxy/4,5-dimethoxybenzylidene)-4-piperidone structure were prepared and analyzed for their cytotoxic impact on eight human cancer cell lines of five different entities. The known 3,4,5-trimethoxybenzylidene curcuminoid 2a and the new bis-(3-bromophenyl) and bis-(3,5-dibromophenyl) derivatives 3c ((E)-1-ethyl-3,5-bis(3-bromo-4,5-dimethoxybenzylidene)-4-piperidone HCl) and 3d ((E)-1-ethyl-3,5-bis(3,5-dibromo-4-methoxybenzylidene)-4-piperidone HCl) proved to be more strongly antiproliferative than the known curcuminoid EF24 against six of these cell lines. Compounds 2a and 3c caused a distinct increase of reactive oxygen species, which eventually elicited apoptosis in 518A2 melanoma cells. Compound 2a arrested 518A2 melanoma cells in G₁ phase of the cell cycle and had no effect on the expression of pro-metastatic matrix metalloproteinases MMP-2 and MMP-9, whereas 3c led to an accumulation of 518A2 cells in the G₂/M phase and to a downregulation of MMP-2 expression. In addition, treatment with 2a and 3c resulted in significant inhibition of colony formation in HCT116 cells. Both 2a and 3c showed antiangiogenic activity, for example, by inhibiting the formation of sub-intestinal veins (SIV) in zebrafish embryos. Compound 3c was also well tolerated by mice and inhibited the growth of HCT116 colon cancer xenografts. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Formula: C8H6Br2O2).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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: C8H6Br2O2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nitric Oxide-Releasing Cyclodextrins was written by Jin, Haibao;Yang, Lei;Ahonen, Mona Jasmine R.;Schoenfisch, Mark H.. And the article was included in Journal of the American Chemical Society in 2018.Synthetic Route of C42H63Br7O28 This article mentions the following:

A series of secondary amine-modified cyclodextrin (CD) derivatives were synthesized with diverse exterior terminal groups (i.e., hydroxyl, Me, methoxyl, and primary amine). Subsequent reaction with nitric oxide (NO) gas under alk. conditions yielded N-diazeniumdiolate-modified CD derivatives Adjustable NO payloads (0.6-2.4 μmol/mg) and release half-lives (0.7-4.2 h) were achieved by regulating both the amount of secondary amine precursors and the functional groups around the NO donor. The bactericidal action of these NO-releasing cyclodextrin derivatives was evaluated against Pseudomonas aeruginosa, a Gram-neg. pathogen with antibacterial activity proving dependent on both the NO payload and exterior modification. Materials containing a high d. of NO donors or primary amines exhibited the greatest ability to eradicate P. aeruginosa. Of the materials prepared, only the primary amine-terminated hepta-substituted CD derivatives exhibited toxicity against mammalian L929 mouse fibroblast cells. The NO donor-modified CD was also capable of delivering promethazine, a hydrophobic drug, thus demonstrating potential as a dual-drug releasing therapeutic. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Synthetic Route of C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Synthetic Route of C42H63Br7O28

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

A Nickel(II)-Mediated Thiocarbonylation Strategy for Carbon Isotope Labeling of Aliphatic Carboxamides was written by Pedersen, Simon S.;Donslund, Aske S.;Mikkelsen, Jesper H.;Bakholm, Oskar S.;Papp, Florian;Jensen, Kim B.;Gustafsson, Magnus B. F.;Skrydstrup, Troels. And the article was included in Chemistry – A European Journal in 2021.Application In Synthesis of 15-Bromopentadecanoic acid This article mentions the following:

A series of pharmaceutically relevant small mols. and biopharmaceuticals bearing aliphatic carboxamides have been successfully labeled with carbon-13. Key to the success of this novel carbon isotope labeling technique is the observation that ¹³C-labeled Ni(II)-acyl complexes, formed from a ¹³CO insertion step with Ni(II)-alkyl intermediates, rapidly react in less than one minute with 2,2′-dipyridyl disulfide to quant. form the corresponding 2-pyridyl thioesters. Either the use of ¹³C-SilaCOgen or ¹³C-COgen allows for the stoichiometric addition of isotopically labeled carbon monoxide. Subsequent one-pot acylation of a series of structurally diverse amines provides the desired ¹³C-labeled carboxamides in good yields. A single electron transfer pathway is proposed between the Ni(II)-acyl complexes and the disulfide providing a reactive Ni(III)-acyl sulfide intermediate, which rapidly undergoes reductive elimination to the desired thioester. By further optimization of the reaction parameters, reaction times down to only 11 min were identified, opening up the possibility of exploring this chem. for carbon-11 isotope labeling. Finally, this isotope labeling strategy could be adapted to the synthesis of ¹³C-labeled liraglutide and insulin degludec, representing two antidiabetic drugs. In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Application In Synthesis of 15-Bromopentadecanoic acid).

15-Bromopentadecanoic acid (cas: 56523-59-2) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Application In Synthesis of 15-Bromopentadecanoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and anion binding properties of multi-phosphonium triarylboranes: selective sensing of cyanide ions in buffered water at pH 7 was written by Song, Ki Cheol;Lee, Kang Mun;Nghia, Nguyen Van;Sung, Woo Young;Do, Youngkyu;Lee, Min Hyung. And the article was included in Organometallics in 2013.Recommanded Product: 2,5-Dibromo-1,3-dimethylbenzene This article mentions the following:

A series of mono-, di-, and tris-phosphonium-substituted triarylboranes, [Mes₂BAr^P]I ([2]I), [MesBAr^P₂]I₂ ([3]I₂), and [BAr^P₃]I₃ ([4]I₃) (Ar^P = 4-MePh₂P⁺-2,6-Me₂C₆H₂), were prepared from the corresponding neutral boranes 2a–4a. The crystal structure of [4]I₃ determined by x-ray diffraction study reveals peripheral decoration of aryl groups with phosphonium moieties. The anion affinity of the cationic boranes for fluoride and cyanide ions was investigated by UV-vis absorption titrations in aqueous solution The triarylboranes, [2]I-[4]I₃ bind both fluoride and cyanide ions in a DMSO/H₂O (7:3 volume/volume) mixture with high binding constants (K). Comparison of the K values of triarylboranes for fluoride reveals that fluorophilicity increases with the increasing number of phosphonium moieties: [2]⁺ (K = 2.3 × 10¹ M^-1) < [3]²⁺ (3.6 × 10⁵ M^-1) < [4]³⁺ (1.0 × 10⁷ M^-1). A similar trend is also observed in the cyanide binding, with K values that are greater by 2-4 orders of magnitude than those in the fluoride binding. These results indicate an apparent additive effect of multiple phosphonium substitutions on the Lewis acidity enhancement of triarylboranes. The triphosphonium borane [4]Cl₃, a water-soluble form of [4]I₃, was further utilized in evaluating the anion affinity in water. While [4]³⁺ is shown to hardly bind fluoride in buffered aqueous solutions at pH 7, it binds cyanide with a high binding constant (1.7 × 10⁷ M^-1). In the experiment, the researchers used many compounds, for example, 2,5-Dibromo-1,3-dimethylbenzene (cas: 100189-84-2Recommanded Product: 2,5-Dibromo-1,3-dimethylbenzene).

2,5-Dibromo-1,3-dimethylbenzene (cas: 100189-84-2) 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. 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.Recommanded Product: 2,5-Dibromo-1,3-dimethylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary