Tag: 100-200

Quality Control of EthylbromofluoroacetateOn March 25, 2021, Fujimoto, Kazuki; Yoshida, Shuhei; Tadano, Genta; Asada, Naoya; Fuchino, Kouki; Suzuki, Shinji; Matsuoka, Eriko; Yamamoto, Takahiko; Yamamoto, Shiho; Ando, Shigeru; Kanegawa, Naoki; Tonomura, Yutaka; Ito, Hisanori; Moechars, Diederik; Rombouts, Frederik J. R.; Gijsen, Harrie J. M.; Kusakabe, Ken-ichi published an article in Journal of Medicinal Chemistry. The article was 《Structure-Based Approaches to Improving Selectivity through Utilizing Explicit Water Molecules: Discovery of Selective β-Secretase (BACE1) Inhibitors over BACE2》. The article mentions the following:

BACE1 is an attractive target for disease-modifying treatment of Alzheimer′s disease. BACE2, having high homol. around the catalytic site, poses a critical challenge to identifying selective BACE1 inhibitors. Recent evidence indicated that BACE2 has various roles in peripheral tissues and the brain, and therefore, the chronic use of nonselective inhibitors may cause side effects derived from BACE2 inhibition. Crystallog. anal. of the nonselective inhibitor verubecestat identified explicit water mols. with different levels of free energy in the S2′ pocket. Structure-based design targeting them enabled the identification of propynyl oxazine 3 with improved selectivity. Further optimization efforts led to the discovery of compound 6 with high selectivity. The cocrystal structures of 7, a close analog of 6, bound to BACE1 and BACE2 confirmed that one of the explicit water mols. is displaced by the propynyl group, suggesting that the difference in the relative water displacement cost may contribute to the improved selectivity. After reading the article, we found that the author used Ethylbromofluoroacetate(cas: 401-55-8Quality Control of Ethylbromofluoroacetate)

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.Quality Control of Ethylbromofluoroacetate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Synthesis, crystal structure and fungicidal activity of 3-chloro-4-(3,4-dichloroisothiazol-5-yl)-5-hydroxy-7-methyl-2H-chromen-2-ones》 was published in Chinese Journal of Structural Chemistry in 2021. These research results belong to Lv, You; Li, Kun; Hao, Ze-Sheng; Kalinina, Tatiana A.; Glukhareva, Tatiana V.; Fan, Zhi-Jin. Application In Synthesis of Ethylbromofluoroacetate The article mentions the following:

3-Chloro-4-(3,4-dichloroisothiazol-5-yl)-5-hydroxy-7-methyl-2H-chromen-2-ones I [R = H, Me, Et, F, Cl] coumarin derivatives, were synthesized by β-ketoester formation and cyclization. Target compound I [R = Cl] was crystallized from methanol for structural identification as monoclinic crystal system, space group C2/c with a = 16.2700(6), b = 7.1801(5), c = 23.4861(10) Å, V = 2742.6(2) Å3, Z = 8, Dc = 1.756 g/cm3, F(000) = 1456 and μ = 0.827 mm-1. 8308 Reflections were collected (6.01≤2θ≤50.05°), of which 2428 were unique (Rint = 0.0432) and used in all calculations The final R = 0.0408 (I > 2σ(I)) and wR = 0.1056 (reflections). In-vitro bioassay indicated that compounds I [R = F, Cl] possessed good activity against Botrytis cinerea, Physalospora piricola, Rhizoctonia solani, and Sclerotinia sclerotiorum with lower EC50 values falling between 0.50 and 4.85μg/mL than that of pos. control osthole with its EC50 values between 7.38 and 74.59μg/mL. In-vivo screening showed that I [R = Cl] exhibited 98% and 95% efficacy against Pseudoperonospora cubensis (Berk. & Curt.) Rostov. at 100 and 50μg/mL, resp. These studies observed that the combination of bioactive substructures of isothiazole with coumarin were an effective way to novel fungicide development. The experimental part of the paper was very detailed, including the reaction process of Ethylbromofluoroacetate(cas: 401-55-8Application In Synthesis of Ethylbromofluoroacetate)

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.Application In Synthesis of Ethylbromofluoroacetate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Application of 3395-91-3In 2018 ,《Metal-Free Thiolation of Imidazopyridines with Functionalized Haloalkanes Using Elemental Sulfur》 was published in Advanced Synthesis & Catalysis. The article was written by Zhang, Jun-Rong; Zhan, Ling-Zhi; Wei, Liang; Ning, Yun-Yun; Zhong, Xiao-Lin; Lai, Jing-Xiong; Xu, Li; Tang, Ri-Yuan. The article contains the following contents:

The assembly of two functional mols. via a sulfur linking atom allowed an access to a diverse array of thioether-containing compounds I [R = Et, CH2CN, n-Bu, etc., R1 = Ph, 4-MeC6H4, 4-FC6H4, etc., R2 = H, Me, F]. This method disclosed a metal-free thiolation of imidazopyridines with a variety of functionalized haloalkanes using elemental sulfur to gave thiolated imidazopyridines I. In addition to this study using Methyl 3-bromopropanoate, there are many other studies that have used Methyl 3-bromopropanoate(cas: 3395-91-3Application of 3395-91-3) was used in this study.

Methyl 3-bromopropanoate(cas: 3395-91-3) belongs to bromides. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Application of 3395-91-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of C4H7BrO2In 2016 ,《Bacterial versus human sphingosine-1-phosphate lyase (S1PL) in the design of potential S1PL inhibitors》 was published in Bioorganic & Medicinal Chemistry. The article was written by Sanllehi, Pol; Abad, Jose-Luis; Casas, Josefina; Bujons, Jordi; Delgado, Antonio. The article contains the following contents:

A series of potential active-site sphingosine-1-phosphate lyase (S1PL) inhibitors have been designed from scaffolds 1 and 2, arising from virtual screening using the X-ray structures of the bacterial (StS1PL) and the human (hS1PL) enzymes. Both enzymes are very similar at the active site, as confirmed by the similar exptl. kinetic constants shown by the fluorogenic substrate RBM13 in both cases. However, the docking scoring functions used probably overestimated the weight of electrostatic interactions between the ligands and key active-site residues in the protein environment, which may account for the modest activity found for the designed inhibitors. In addition, the possibility that the inhibitors do not reach the enzyme active site should not be overlooked. Finally, since both enzymes show remarkable structural differences at the access channel and in the proximity to the active site cavity, caution should be taken when designing inhibitors acting around that area, as evidenced by the much lower activity found in StS1PL for the potent hS1PL inhibitor D. In the experiment, the researchers used Methyl 3-bromopropanoate(cas: 3395-91-3Synthetic Route of C4H7BrO2)

Methyl 3-bromopropanoate(cas: 3395-91-3) belongs to bromides. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Synthetic Route of C4H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Quality Control of Ethyl 4-bromobutyrateIn 2019 ,《A Scalable Total Synthesis of Halofuginone》 was published in Organic Process Research & Development. The article was written by Xu, Hua; Yin, Wenhao; Liang, Haoqiang; Nan, Yanbo; Qiu, Fayang; Jin, Yehua. The article contains the following contents:

A scalable total synthesis of halofuginone (I) has been accomplished. This synthetic route features a total of 12 steps of highly efficient reactions, without any chromatog. purification Halofuginone was obtained in 17% overall yield and over 98.5% HPLC purity. All the reaction conditions are mild and reliable. In addition, no hazardous materials are used or produced. All reagents are com. available and inexpensive. This route is safe, robust, scalable, cost-effective, and environmentally benign.Ethyl 4-bromobutyrate(cas: 2969-81-5Quality Control of Ethyl 4-bromobutyrate) was used in this study.

Ethyl 4-bromobutyrate(cas: 2969-81-5) belongs to bromides. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Quality Control of Ethyl 4-bromobutyrate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Fusaric acid and derivatives as novel antimicrobial agents》 was written by Thanh, Tung Truong; Quoc, Thang Nguyen; Xuan, Huy Luong. Formula: C4H7Br And the article was included in Medicinal Chemistry Research in 2020. The article conveys some information:

Abstract: The synthesis and screening of several fusaric acid (FA) and analogs against five common clin. pathogens (gram-pos. and gram-neg.) and in vitro hemolytic activity assay in human red blood cells, for the first time, were reported. The biol. results reveal that FA and its analogs exhibited moderate antimicrobial activities. Compounds 2-5 and 7 showed growth inhibitory activity in gram-pos. bacteria. Compounds 6 and 9 showed growth inhibitory activity in both gram-pos. and gram-neg. bacteria. None of the compounds induce hemolysis, which is potent for future drug development on this template. In addition, the structure-activity relationship and docking studies are discussed. After reading the article, we found that the author used (Bromomethyl)cyclopropane(cas: 7051-34-5Formula: C4H7Br)

(Bromomethyl)cyclopropane(cas: 7051-34-5) is used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.Formula: C4H7Br

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Efficient Oral Delivery of Poorly Water-Soluble Drugs Using Carnitine/Organic Cation Transporter 2-Mediated Polymeric Micelles》 was published in ACS Biomaterials Science & Engineering in 2020. These research results belong to He, Chuyu; Jin, Yao; Deng, Yunqiang; Zou, Yang; Han, Shidi; Zhou, Chuhang; Zhou, Yuanhang; Liu, Yan. HPLC of Formula: 539-74-2 The article mentions the following:

The intestine epithelium is considered to be the most critical obstacle for nanoparticles for oral delivery of water-insoluble and poorly absorbed drugs. Based on the specific transporters located on the apical membrane of the intestinal epithelium, the carnitine-conjugated polymeric micelles targeting to the carnitine/organic cation transporter 2 (OCTN2) were developed by combining carnitine-conjugated poly(2-ethyl-2-oxazoline)-poly(D,L-lactide) with monomethoxy poly(ethylene-glycol)-poly(D,L-lactide). The carnitine-conjugated micelles with favorable stability in gastrointestinal fluid were validated to remarkably increase the cellular internalization and transcellular transport, while these were not the cases in the presence of free carnitine. These were further confirmed by more distribution of the micelles within epithelial cells, on the apical and basolateral side of the epithelium in mice. Addnl., identification of the carnitine-conjugated micelles by OCTN2 was detected to facilitate cellular uptake of the micelles via fluorescence immunoassay. Both clathrin and caveolae/lipid rafts pathways mediated endocytosis and transcellular transport of the carnitine-conjugated micelles, implying the enrichment of endocytic and transcellular transport pathway compared with that of carnitine-unconjugated micelles. Further, the intracellular trafficking process of the carnitine-conjugated micelles was tracked under confocal laser scanning microscopy, which involved in intracellular compartments such as late endosomes, lysosomes, endoplasmic reticulum, and Golgi apparatus as well. In conclusion, the current study provided an efficient strategy to facilitate the oral absorption of water-insoluble and poorly absorbed agents using intestinal transporter-mediated polymeric micelles. After reading the article, we found that the author used Ethyl 3-bromopropanoate(cas: 539-74-2HPLC of Formula: 539-74-2)

Ethyl 3-bromopropanoate(cas: 539-74-2) belongs to organobromine compounds.Depending on the type of carbon to which the bromine is bonded, organic bromide could be alkyl, alkenyl, alkynyl, or aryl. Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides. HPLC of Formula: 539-74-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《A green and highly effective protocol for the synthesis of N,N’-alkylidene bisamides using saccharin-N-sulfonic acid》 was published in Iranian Chemical Communication in 2020. These research results belong to Zare, Abdolkarim; Dianat, Manije; Pishahang, Nasrin; Khanivar, Roghayyeh; Kaman-Torki, Soheila; Fakhraei, Fatemeh; Kordrostami, Zahra; Sadeghi-Takallo, Masoud. COA of Formula: C7H5BrO The article mentions the following:

A green and highly effective solvent-free protocol has been reported for the synthesis of N,N’-alkylidene bisamides RC(O)NHCH(Ar)NHC(O)R (R = Me, Ph; Ar = Ph, 3-O2NC6H4, 4-BrC6H4, etc.) via the reaction of arylaldehydes (1 equivalent) with primary amides (2 equivalent) in the presence of saccharin-N-sulfonic acid (SaSA) as a solid-acid catalyst. The mentioned compounds have been obtained in high yields and short reaction times. In the part of experimental materials, we found many familiar compounds, such as o-Bromobenzaldehyde(cas: 6630-33-7COA of Formula: C7H5BrO)

o-Bromobenzaldehyde(cas: 6630-33-7) is used in L-threonine aldolase-catalyzed enantio/diastereoselective aldol reactions.COA of Formula: C7H5BrOIt is a key starting material in the total synthesis of an anticancer agent, (-)-taxol.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Enzymatic assembly of carbon-carbon bonds via iron-catalysed sp3 C-H functionalization》 were Zhang, Ruijie K.; Chen, Kai; Huang, Xiongyi; Wohlschlager, Lena; Renata, Hans; Arnold, Frances H.. And the article was published in Nature (London, United Kingdom) in 2019. HPLC of Formula: 539-74-2 The author mentioned the following in the article:

Although abundant in organic mols., carbon-hydrogen (C-H) bonds are typically considered unreactive and unavailable for chem. manipulation. Recent advances in C-H functionalization technol. have begun to transform this logic, while emphasizing the importance of and challenges associated with selective alkylation at a sp3 carbon. Here we describe iron-based catalysts for the enantio-, regio- and chemoselective intermol. alkylation of sp3 C-H bonds through carbene C-H insertion. The catalysts, derived from a cytochrome P 450 enzyme in which the native cysteine axial ligand has been substituted for serine (cytochrome P411), are fully genetically encoded and produced in bacteria, where they can be tuned by directed evolution for activity and selectivity. That these proteins activate iron, the most abundant transition metal, to perform this chem. provides a desirable alternative to noble-metal catalysts, which have dominated the field of C-H functionalization. The laboratory-evolved enzymes functionalize diverse substrates containing benzylic, allylic or α-amino C-H bonds with high turnover and excellent selectivity. Furthermore, they have enabled the development of concise routes to several natural products. The use of the native iron-haem cofactor of these enzymes to mediate sp3 C-H alkylation suggests that diverse haem proteins could serve as potential catalysts for this abiol. transformation, and will facilitate the development of new enzymic C-H functionalization reactions for applications in chem. and synthetic biol. The experimental process involved the reaction of Ethyl 3-bromopropanoate(cas: 539-74-2HPLC of Formula: 539-74-2)

Ethyl 3-bromopropanoate(cas: 539-74-2) 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. HPLC of Formula: 539-74-2 Moreover, several studies demonstrate that the average proportion of bromine in drugs is significantly higher than that in natural products.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2018,Journal of Organic Chemistry included an article by Frayne, Stephen H.; Northrop, Brian H.. Reference of Methyl 3-bromopropanoate. The article was titled 《Evaluating Nucleophile Byproduct Formation during Phosphine- and Amine-Promoted Thiol-Methyl Acrylate Reactions》. The information in the text is summarized as follows:

The commonly accepted mechanism of nucleophile-initiated thiol-acrylate reactions requires the formation of undesired nucleophile byproducts. A systematic evaluation of the formation of such nucleophile byproducts has been carried out to understand the relationships between byproduct formation and nucleophile structure, stoichiometry, solvent, and reaction type. Three common nucleophiles for thiol-Michael reactions were investigated: dimethylphenylphosphine (DMPP), diethylamine (DEA), and hexylamine (HA). The formation of phosphonium ester and aza-Michael byproducts upon initiating a representative thiol-acrylate reaction between 1-hexanethiol and Me acrylate at a range of initiator loading (0.01-10.0 equiv) and in different solvents (neat, DMSO, THF, and CHCl3) was determined by 1H NMR spectroscopy. The influence of reaction type was investigated by expanding from small mol. reactions to end group thiol-acrylate functionalization of PEG-diacrylate polymers and through investigations of polymer-polymer coupling reactions. Results indicate that the propensity of forming nucleophile byproducts varies with nucleophile type, solvent, and reaction type. Interestingly, for all but polymer-polymer ligation reactions, nucleophile byproduct formation is largely unobserved for nitrogen-centered nucleophiles DEA and HA and essentially nonexistent for the phorphorous-centered nucleophile DMPP. A rationale for the differences in nucleophile byproduct formation for DMPP, DEA, and HA is proposed and supported by exptl. and computational anal. After reading the article, we found that the author used Methyl 3-bromopropanoate(cas: 3395-91-3Reference of Methyl 3-bromopropanoate)

Methyl 3-bromopropanoate(cas: 3395-91-3) belongs to bromides. 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.Reference of Methyl 3-bromopropanoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary