Month: October 2022

《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

《Zinc/Indium Bimetallic Lewis Acid Relay Catalysis for Dehydrogenative Silylation/Hydrosilylation Reaction of Terminal Alkynes with Bis(hydrosilane)s》 was written by Tani, Tomohiro; Sohma, Yudai; Tsuchimoto, Teruhisa. Reference of Indium(III) bromideThis research focused onzinc indium Lewis acid catalyst dehydrogenative silylation alkyne hydrosilane; disilanaphthalene preparation; disilaindane preparation; disilylalkene preparation; hydrosilylation intramol dehydrogenative silylation zinc indium catalyst; bismuth catalyzed Hiyama cross coupling ether formation iododesilylation. The article conveys some information:

When mixed with two different Lewis acid catalysts of Zn and In, terminal alkynes react with bis(hydrosilane)s to selectively provide 1,1-disilylalkenes from among several possible products, by way of a sequential dehydrogenative silylation/intramol. hydrosilylation reaction. Adding a pyridine base is crucial in this reaction; a switch as a catalyst of the Zn Lewis acid is turned on by forming a Zn-pyridine-base complex. A range of the 1,1-disilylalkenes can be obtained by a combination of aryl and aliphatic terminal alkynes plus aryl-, heteroaryl-, and naphthyl-tethered bis(hydrosilane)s. The 1,1-disilylalkene prepared here is available as a reagent for further transformations by using its C-Si or C:C bond. The former includes Hiyama cross-coupling, Bi-catalyzed ether formation, and iododesilylation; the latter includes double alkylation and epoxidation Mechanistic studies clarified the role of the two Lewis acids: the Zn-pyridine-base complex catalyzes the dehydrogenative silylation as a 1st stage, and, following on this, the In Lewis acid catalyzes the ring-closing hydrosilylation as a 2nd stage, thus leading to the 1,1-disilylalkene. The experimental part of the paper was very detailed, including the reaction process of Indium(III) bromide(cas: 13465-09-3Reference of Indium(III) bromide)

Indium(III) bromide(cas: 13465-09-3) is used in organic synthesis as a water tolerant Lewis acid. It efficiently catalyzes the three-component coupling of β-keto esters, aldehydes and urea (or thiourea) to afford the corresponding dihydropyrimidinones.Reference of Indium(III) bromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of C11H13BrO2On September 30, 1991 ,《Interphenylene 7-oxabicyclo[2.2.1]heptane thromboxane A2(TxA2)antagonists. Semicarbazone ω-chains》 was published in Journal of Medicinal Chemistry. The article was written by Misra, Raj N.; Brown, Baerbel R.; Han, Wen Ching; Harris, Don N.; Hedberg, Anders; Webb, Maria L.; Hall, Steven E.. The article contains the following contents:

A series of chiral interphenylene oxabicycloheptane semicarbazones I [n = 1, 2; X = CH2, OCH2, (CH2)2, (CH2)3] were prepared and evaluated for their in vitro thromboxane (TxA2) antagonist activity and in vivo duration of action. The potency of I was highly dependent on the substitution pattern of the interphenylene ring and decreased in the order ortho > meta > para. (S)-I [n = 1; X = (CH2)2 (II)] (SQ 35,091) was identified as a potent and long-acting TxA2 antagonist. In human platelet rich plasma II inhibited arachidonic acid (800 μM) and U-46,619 (10 μM) induced aggregation with T50 values of 3 and 12 nM, resp. In contrast, no inhibition of ADP (20 μM) induced aggregation was observed at >1000 μM. Receptor binding studies with [3H]-SQ 29,548 showed II was a competitive antagonist with a Kd value of 1.0 ± 0.1 nM in human platelet membranes. In vivo II (0.2 mg/kg po) showed extended protection (T50 = 16 h) from U-46,619 (2 mg/kg i.v.) induced death in mice. These compounds have for the 1st time demonstrated that a metabolically stable interphenylene α side chain can be introduced into a prostanoid-like series of TxA2 antagonists with the maintenance of potent antagonist activity. In the experimental materials used by the author, we found Ethyl 3-(2-bromophenyl)propanoate(cas: 135613-33-1Synthetic Route of C11H13BrO2)

Ethyl 3-(2-bromophenyl)propanoate(cas: 135613-33-1) 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. Synthetic Route of C11H13BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

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

In 2014,Carbain, Benoit; Paterson, David J.; Anscombe, Elizabeth; Campbell, Allyson J.; Cano, Celine; Echalier, Aude; Endicott, Jane A.; Golding, Bernard T.; Haggerty, Karen; Hardcastle, Ian R.; Jewsbury, Philip J.; Newell, David R.; Noble, Martin E. M.; Roche, Celine; Wang, Lan Z.; Griffin, Roger J. published 《8-Substituted O6-Cyclohexylmethylguanine CDK2 Inhibitors: Using Structure-Based Inhibitor Design to Optimize an Alternative Binding Mode》.Journal of Medicinal Chemistry published the findings.HPLC of Formula: 76006-33-2 The information in the text is summarized as follows:

Evaluation of the effects of purine C-8 substitution within a series of CDK1/2-selective O6-cyclohexylmethylguanine derivatives revealed that potency decreases initially with increasing size of the alkyl substituent. Structural anal. showed that C-8 substitution is poorly tolerated, and to avoid unacceptable steric interactions, these compounds adopt novel binding modes. Thus, 2-amino-6-cyclohexylmethoxy-8-isopropyl-9H-purine adopts a “”reverse”” binding mode where the purine backbone has flipped 180°. This provided a novel lead chemotype from which we have designed more potent CDK2 inhibitors using, in the first instance, quantum mech. energy calculations Introduction of an ortho-tolyl or ortho-chlorophenyl group at the purine C-8 position restored the potency of these “”reverse”” binding mode inhibitors to that of the parent 2-amino-6-cyclohexylmethoxy-9H-purine. By contrast, the corresponding 8-(2-methyl-3-sulfamoylphenyl)-purine derivative exhibited submicromolar CDK2-inhibitory activity by virtue of engineered addnl. interactions with Asp86 and Lys89 in the reversed binding mode, as confirmed by X-ray crystallog. In addition to this study using 3-Bromo-2-methylbenzoic acid, there are many other studies that have used 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2HPLC of Formula: 76006-33-2) was used in this study.

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. HPLC of Formula: 76006-33-2 The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2015,Pogrebnoi, Vsevolod published 《New N-glucosylated substituted anilines》.Chemistry Journal of Moldova published the findings.Quality Control of 3,5-Dibromoaniline The information in the text is summarized as follows:

The reaction of (+)-D-glucose 1 with 4-chloroaniline 6b or 3,5-dibromoaniline 12 leads almost exclusively to the β-configuration of N-glucosylated anilines 7b and 13. Acetylated derivatives 8b, 14 and 15 were obtained by dissolving/suspending substances 7b and 13 in Ac2O/Py mixture The acetylation of 2-(3,5-dibromophenylamino)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 13 is less selective than in the case of the 2-(4-chlorophenylamino)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 7b and leads to compounds 2-(acetoxymethyl)-6-(3,5-dibromophenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate 14 and 2-(acetoxymethyl)-6-(3,5-dibromophenylamino)-5-hydroxytetrahydro-2H-pyran-3,4-diyl diacetate 15 in a 2:1 ratio. The product 14 is formed with greater selectivity and in a higher yield (up to 80%) when the reaction is catalyzed by DMAP and stored for one week at +4°C. The results came from multiple reactions, including the reaction of 3,5-Dibromoaniline(cas: 626-40-4Quality Control of 3,5-Dibromoaniline)

3,5-Dibromoaniline(cas: 626-40-4) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.Quality Control of 3,5-Dibromoaniline

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2016,Liang, Guodong; Wang, Huixin; Chong, Huihui; Cheng, Siqi; Jiang, Xifeng; He, Yuxian; Wang, Chao; Liu, Keliang published 《An effective conjugation strategy for designing short peptide-based HIV-1 fusion inhibitors》.Organic & Biomolecular Chemistry published the findings.Product Details of 1129-28-8 The information in the text is summarized as follows:

Lengthy peptides corresponding to the C-terminal heptad repeat (C-peptides) of human immunodeficiency virus type 1 (HIV-1) gp41 are potent inhibitors against virus-cell fusion. Designing short C-peptide-based HIV-1 fusion inhibitors could potentially redress the physicochem. and tech. liabilities of a long-peptide therapeutic. However, designing such inhibitors with high potency has been challenging. We generated a conjugated architecture by incorporating small-mol. inhibitors of gp41 into the N-terminus of a panel of truncated C-peptides. Among these small mol.-capped short peptides, the 26-residue peptide Indole-T26 inhibited HIV-1 Env-mediated cell-cell fusion and viral replication at low nanomolar levels, reaching the potency of the only clin. used 36-residue peptide T20 (enfuvirtide). Collectively, our work opens up a new avenue for developing short peptide-based HIV-1 fusion inhibitors, and may have broad applicability to the development of modulators of other class I fusion proteins. The results came from multiple reactions, including the reaction of Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8Product Details of 1129-28-8)

Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides.Product Details of 1129-28-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2017,Su, Bo; Hartwig, John F. published 《Ir-Catalyzed enantioselective, intramolecular silylation of methyl C-H Bonds》.Journal of the American Chemical Society published the findings.Recommanded Product: 7073-94-1 The information in the text is summarized as follows:

2-Isopropylphenyl hydrosilanes undergo intramol. silylative asym. cyclization, catalyzed by iridium chiral oxazolinylpyridine and oxazolinylquinoline complexes, giving chiral 3-methyl-1-silaindanes with >95% enantioselectivity, the dehydrogenative coupling being promoted by addition of hydrogen acceptors, 3,3-dimethyl-1-butene or norbornene. We report highly enantioselective intramol., silylations of unactivated, primary C(sp3)-H bonds. The reactions form dihydrobenzosiloles in high yields with excellent enantioselectivities by functionalization of enantiotopic Me groups under mild conditions. The reaction is catalyzed by an iridium complex generated from [Ir(COD)OMe]2 and chiral dinitrogen ligands that we recently disclosed. The C-Si bonds in the enantioenriched dihydrobenzosiloles were further transformed to C-Cl, C-Br, C-I, and C-O bonds in final products. The potential of this reaction was illustrated by sequential C(sp3)-H and C(sp2)-H silylations and functionalizations, as well as diastereoselective C-H silylations of a chiral, natural-product derivative containing multiple types of C-H bonds. Preliminary mechanistic studies suggest that C-H cleavage is the rate-determining step. The experimental process involved the reaction of 1-Bromo-2-isopropylbenzene(cas: 7073-94-1Recommanded Product: 7073-94-1)

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.Recommanded Product: 7073-94-1 Organobromine compounds have fallen under increased scrutiny for their environmental impact.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2017,Joergensen, Lars; Al-Khawaja, Anas; Kickinger, Stefanie; Vogensen, Stine B.; Skovgaard-Petersen, Jonas; Rosenthal, Emil; Borkar, Nrupa; Loffler, Rebekka; Madsen, Karsten K.; Brauner-Osborne, Hans; Schousboe, Arne; Ecker, Gerhard F.; Wellendorph, Petrine; Clausen, Rasmus P. published 《Structure-Activity Relationship, Pharmacological Characterization, and Molecular Modeling of Noncompetitive Inhibitors of the Betaine/γ-Aminobutyric Acid Transporter 1 (BGT1)》.Journal of Medicinal Chemistry published the findings.Application of 1129-28-8 The information in the text is summarized as follows:

N-(1-Benzyl-4-piperidinyl)-2,4-dichlorobenzamide (BPDBA) is a noncompetitive inhibitor of the betaine/GABA transporter 1 (BGT1). The authors here report the synthesis and structure-activity relationship of 71 analogs. The authors identify I as a more soluble 2,4-Cl substituted 3-pyridine analog with retained BGT1 activity and an improved off-target profile compared to BPDBA. The authors performed radioligand-based uptake studies at chimeric constructs between BGT1 and GAT3, experiments with site-directed mutated transporters, and computational docking in a BGT1 homol. model based on the newly determined x-ray crystal structure of the human serotonin transporter (hSERT). On the basis of these experiments, the authors propose a binding mode involving residues within TM10 in an allosteric site in BGT1 that corresponds to the allosteric binding pocket revealed by the hSERT crystal structure. The study provides first insights into a proposed allosteric binding pocket in BGT1, which accommodates the binding site for a series of novel noncompetitive inhibitors. The experimental part of the paper was very detailed, including the reaction process of Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8Application of 1129-28-8)

Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. Application of 1129-28-8 The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2017,Nikodemiak, Paul; Koert, Ulrich published 《Metal-Catalyzed Synthesis of Functionalized 1,2,4-Oxadiazoles from Silyl Nitronates and Nitriles》.Advanced Synthesis & Catalysis published the findings.Electric Literature of C9H9BrO2 The information in the text is summarized as follows:

The metal-catalyzed cycloaddition of silyl nitronates and nitriles leading to 1,2,4-oxadiazoles I [R = Me, 1-cyclohexene, Ph, etc.; R1 = Me, CH2Cl, CO2Me, etc.] was described. Silver(I) triflate (AgOTf) and ytterbium(III) triflate [Yb(OTf)3] were the suitable catalysts. A variety of functional groups was tolerated in the nitrile. The reaction worked well for alkenyl and aryl silyl nitronates while the use of alkyl silyl nitronates was less efficient. Mechanistic studies were in favor of an elimination of tert-butyl(dimethyl)silanol (TBSOH) after the cycloaddition step. This new approach was also applied for the synthesis of the drug ataluren. In the part of experimental materials, we found many familiar compounds, such as Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8Electric Literature of C9H9BrO2)

Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. The most pervasive is the naturally produced bromomethane.Electric Literature of C9H9BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary