Month: February 2023

Synthesis and biological evaluation of sulforaphane derivatives as potential antitumor agents was written by Hu, Kun;Qi, Yan-jie;Zhao, Juan;Jiang, He-fei;Chen, Xin;Ren, Jie. And the article was included in European Journal of Medicinal Chemistry in 2013.Safety of N-(5-Bromopentyl)phthalimide This article mentions the following:

A series of sulforaphane derivatives, S:C:NCH₂(CH₂)_nCH₂X(O)R [I, R = PhCH₂, Et, 2-furanylmethyl, cyclopentyl, etc., X = S(O), n = 1-4; R = PhCH₂, X = S, n = 2; R = PhCH₂, X = SO₂, n = 2], were synthesized and evaluated in vitro for their cytotoxicity against five cancer cell lines (HepG2, A549, MCF-7, HCT-116 and SH-SY5Y). The pharmacol. results showed that many of the derivatives displayed more potent cytotoxicity than sulforaphane (SFN). Furthermore, SFN and derivative I [R = PhCH₂, X = S(O), n = 2] (II) could induce cell cycle arrest at S or G2/M phase and cell apoptosis. SFN and II exhibited time- and dose-dependent activation on Nrf2 transcription factor, and II acted as a more potent Nrf2 inducer than SFN. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Safety of N-(5-Bromopentyl)phthalimide).

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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Safety of N-(5-Bromopentyl)phthalimide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design, synthesis and structure-activity relationship evaluation of novel LpxC inhibitors as Gram-negative antibacterial agents was written by Ding, Shi;Dai, Rui-Yang;Wang, Wen-Ke;Cao, Qiao;Lan, Le-Fu;Zhou, Xian-Li;Yang, Yu-She. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2018.Name: Methyl 4-bromo-2-fluorobenzoate This article mentions the following:

LpxC inhibitors are new-type antibacterial agents developed in the last twenty years, mainly against Gram-neg. bacteria infections. To develop novel LpxC inhibitors with good antibacterial activities and biol. metabolism, the authors summarized the basic skeleton of reported LpxC inhibitors, designed and synthesized several series of compounds and tested their antibacterial activities against Escherichia coli and Pseudomonas aeruginosa in vitro. Structure-activity relations are discussed. The metabolism stability of YDL-2, YDL-5, YDL-8, YDL-14, YDL-20-YDL-23 were evaluated in liver microsomes, which indicated that the 2-amino iso-Pr group may be a preferred structure than the 2-hydroxy Et group in the design of LpxC inhibitors. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2Name: Methyl 4-bromo-2-fluorobenzoate).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) 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. 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: Methyl 4-bromo-2-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

On-Surface Debromination of 2,3-Bis(dibromomethyl)- and 2,3-Bis(bromomethyl)naphthalene: Dimerization or Polymerization? was written by Tang, Yanning;Ejlli, Barbara;Niu, Kaifeng;Li, Xuechao;Hao, Zhengming;Xu, Chaojie;Zhang, Haiming;Rominger, Frank;Freudenberg, Jan;Bunz, Uwe H. F.;Muellen, Klaus;Chi, Lifeng. And the article was included in Angewandte Chemie, International Edition in 2022.Electric Literature of C4H4BrNO2 This article mentions the following:

We describe the on-surface dehalogenative homocoupling of benzylic bromides, namely bis-bromomethyl- and bis-gem-(dibromomethyl) naphthalene as a potential route to either hydrocarbon dimers or conjugated polymers on Au(111). While bis-gem-(dibromomethyl) naphthalene affords different dimers with naphthocyclobutadiene as the key intermediate, bis-bromomethyl naphthalene furnishes a poly(o-naphthylene vinylidene) as a non-conjugated polymer which undergoes dehydrogenation toward its conjugated derivative poly(o-naphthylene vinylene) upon mild annealing. A combination of scanning tunneling microscopy, non-contact at. force microscopy and d. functional theory calculations provides deep insights into the prevailing mechanisms. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Electric Literature of C4H4BrNO2).

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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Electric Literature of C4H4BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Domino recombinant γ-isomerization and reverse Wacker oxidation of γ-vinyl-γ-butyrolactone: Synthesis of (+)-trans-, (-)- and (+)-disparlures was written by Bethi, Venkati;Kattanguru, Pullaiah;Fernandes, Rodney A.. And the article was included in European Journal of Organic Chemistry in 2014.Recommanded Product: Isopentyltriphenylphosphonium bromide This article mentions the following:

A domino Pd-catalyzed recombinant γ-isomerization and reverse Wacker oxidation of γ-vinyl-γ-butyrolactone was explored. The strategy was used in the stereoselective synthesis of (+)-trans-, (-)- and (+)-disparlure. The synthesis was achieved in 7-8 steps from D-glucono-δ-lactone with overall yields of 19.3, 20.7, and 22.6%, resp. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Recommanded Product: Isopentyltriphenylphosphonium bromide).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) 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.Recommanded Product: Isopentyltriphenylphosphonium bromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Systematic Investigation of Halogen Bonding in Protein-Ligand Interactions was written by Hardegger, Leo A.;Kuhn, Bernd;Spinnler, Beat;Anselm, Lilli;Ecabert, Robert;Stihle, Martine;Gsell, Bernard;Thoma, Ralf;Diez, Joachim;Benz, Joerg;Plancher, Jean-Marc;Hartmann, Guido;Banner, David W.;Haap, Wolfgang;Diederich, Francois. And the article was included in Angewandte Chemie, International Edition in 2011.Name: 1-(4-Bromo-2-fluorophenyl)cyclopropanecarboxylic acid This article mentions the following:

Halogen bonding triggers activity. Increasing binding affinity was observed for a series of covalent human Cathepsin L inhibitors by exchanging an aryl ring H atom with Cl, Br, and I, which undergo halogen bonding with the C=O group of Gly61 in the S3 pocket of the enzyme. Fluorine, in contrast, strongly avoids halogen bonding. The strong distance and angle dependence of halogen bonding was confirmed for biol. systems. In the experiment, the researchers used many compounds, for example, 1-(4-Bromo-2-fluorophenyl)cyclopropanecarboxylic acid (cas: 872422-15-6Name: 1-(4-Bromo-2-fluorophenyl)cyclopropanecarboxylic acid).

1-(4-Bromo-2-fluorophenyl)cyclopropanecarboxylic acid (cas: 872422-15-6) 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). 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-(4-Bromo-2-fluorophenyl)cyclopropanecarboxylic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

N,C-Disubstituted Biarylpalladacycles as Precatalysts for ppm Pd-Catalyzed Cross Couplings in Water under Mild Conditions was written by Thakore, Ruchita R.;Takale, Balaram S.;Gallou, Fabrice;Reilly, John;Lipshutz, Bruce H.. And the article was included in ACS Catalysis in 2019.Recommanded Product: Methyl 4-bromo-2-fluorobenzoate This article mentions the following:

Various mono- and di-substitution patterns on the parent biarylamine skeleton characteristic of palladacycles, as well as the counterion effect, have been studied looking to increase the effectiveness of the catalyst formed under micellar catalysis conditions in water, with the goal of reducing the amount of Pd needed for coupling reactions. Several substituted palladacycles containing readily accessible ligands were chosen for evaluation. The results indicate that: (1) pre-activation of Pd(II) salts as precursors for Suzuki-Miyaura (SM) couplings via treatment with a reducing agent is not required; (2) reactions could be performed with ca. half the loading of Pd relative to that previously required based on a combination of a Pd(II) salt and ligand; (3) the most effective palladacycle pre-catalyst has been identified as that containing an iso-Pr group on both an aryl ring and on nitrogen, together with the ligand EvanPhos and triflate as the counterion. This pre-catalyst is also effective in other C-C bond forming reactions, such as Heck and Sonogashira couplings. No organic solvents were needed for these processes, while the aqueous reaction medium could be recycled several times. A 1-pot, 4-step sequence involving Suzuki-Miyaura, reduction, alkylation, and acylation reactions highlights the potential for this pre-catalyst to maximize synthetic gain while minimizing costs and waste generation. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2Recommanded Product: Methyl 4-bromo-2-fluorobenzoate).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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: Methyl 4-bromo-2-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Radical trifunctionalization of hexenenitrile via remote cyano migration was written by Chang, Chenyang;Zhang, Huihui;Wu, Xinxin;Zhu, Chen. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.Category: bromides-buliding-blocks This article mentions the following:

A novel radical-mediated trifunctionalization of hexenenitriles via the strategy of remote functional group migration is disclosed. A portfolio of functionalized hexenenitriles are employed as substrates. After difunctionalization of the unactivated alkenyl part via remote cyano migration, the in situ formed radical intermediate is captured by an azido radical, thus enabling the trifunctionalization. The reaction features mild conditions and broad functional group compatibility, leading to valuable products bearing multiple useful groups. This protocol further extends the scope of remote functional group migration. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Category: bromides-buliding-blocks).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) 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. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of S-alkylisothiuronium halides by reaction of thiourea with ω-(4-hydroxyaryl)alkyl halides was written by Kandalintseva, N. V.;Prosenko, A. E.;Dyubchenko, O. I.;Stoyanov, E. S.. And the article was included in Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) in 2001.Category: bromides-buliding-blocks This article mentions the following:

A number of new S-arylalkylisothiuronium salts, e.g., I, were synthesized by reaction of ω-[4-hydroxy(methoxy)aryl]alkyl halides with thiourea. The resulting isothiuronium salts in aqueous solution react with sodium (potassium) halides to form halogen exchange products. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Category: bromides-buliding-blocks).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Conjugated Dienes as Prohaptens in Contact Allergy: In Vivo and in Vitro Studies of Structure-Activity Relationships, Sensitizing Capacity, and Metabolic Activation was written by Bergstroem, Moa Andresen;Luthman, Kristina;Nilsson, J. Lars G.;Karlberg, Ann-Therese. And the article was included in Chemical Research in Toxicology in 2006.Recommanded Product: Isopentyltriphenylphosphonium bromide This article mentions the following:

There is a great interest in developing in vitro/in silico methods for the prediction of contact allergenic activity. However, many proposed methods do not take the activation of prohaptens to sensitizers by skin metabolism into account. As a consequence, consumer products containing potent sensitizers could be marketed. To identify prohaptens, studies regarding their structure-activity relationships and the mechanisms of their activation must be conducted. In the present investigation, we have studied the structure-activity relationships for alkene prohaptens. A series of seven alkenes (1-7), all of the same basic structure but with variation in the number and position(s) of the double bond(s), were designed and screened for sensitizing capacity using the murine local lymph node assay. Compounds 1-7 were also incubated with liver microsomes in the presence of glutathione to trap and identify reactive metabolites. The metabolic conversion of three alkenes (9-11) to epoxides (12-15) was also studied along with comparison of their sensitizing capacity. Our results show that conjugated dienes in or in conjunction with a six-membered ring are prohaptens that can be metabolically activated to epoxides and conjugated with GSH. Related alkenes containing isolated double bonds and an acyclic conjugated diene were shown to be weak or nonsensitizers. For the first time, the naturally occurring monoterpenes α-phellandrene, β-phellandrene, and α-terpinene were demonstrated to be prohaptens able to induce contact allergy. The difference in sensitizing capacity of conjugated dienes as compared to alkenes with isolated double bonds was found to be due to the high reactivity and sensitizing capacity of the allylic epoxides metabolically formed from conjugated dienes. We recommend that these structure-activity relationship rules are incorporated into in silico predictive databases and propose that the prediction of contact allergenic activity of suspected prohaptens is based on assessment of susceptibility to metabolic activation and chem. reactivity of potential metabolites. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Recommanded Product: Isopentyltriphenylphosphonium bromide).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) 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.Recommanded Product: Isopentyltriphenylphosphonium bromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Facile, direct reaction of benzaldehydes to 3-arylprop-2-enoic acids and 3-arylprop-2-ynoic acids in aqueous medium was written by Thiemann, Thies;Elshorbagy, Mohamed W.;Salem, Mostafa H. F. A.;Ahmadani, Siraj A. N.;Al-Jasem, Yosef;Al Azani, Mariam;Al-Sulaibi, Mazen A. M.;Al-Hindawi, Bassam. And the article was included in International Journal of Organic Chemistry in 2016.Recommanded Product: 3,5-Dibromo-4-methoxybenzaldehyde This article mentions the following:

Wittig reactions of benzaldehydes, alkanals, and cycloalkanals as well as of acetophenones are carried out with alkoxycarbonyl methylidenetriphenylphosphoranes in 10 w% aqueous NaOH, where the cinnamates and alkenoates produced are hydrolyzed in situ and the corresponding acids are obtained after mostly simple extractive work-up, often without employing organic solvents. Under the same conditions, benzaldehydes are reacted with alkoxycarbonyl bromomethylidenephosphorane to produce 3-arylprop-2-ynoic acids (arylpropiolic acids). In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Recommanded Product: 3,5-Dibromo-4-methoxybenzaldehyde).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) 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). 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.Recommanded Product: 3,5-Dibromo-4-methoxybenzaldehyde

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary