Month: October 2022

The author of 《A novel finding of nalbuphine-6-glucuronide, an active opiate metabolite, possessing potent antinociceptive effects: Synthesis and biological evaluation》 were Liang, Ren-Jong; Lai, Yen-Hsun; Kao, Yu-Ting; Yang, Ting-Hsuan; Chen, Yen-Lun; Wang, Hong-Jaan. And the article was published in European Journal of Medicinal Chemistry in 2019. Related Products of 21085-72-3 The author mentioned the following in the article:

Nalbuphine, a partial agonist/antagonist opioid analgesic, is structurally related to morphine. It is equipotent to morphine and has no serious side effects. In the past few decades, studies focusing on morphine metabolism have indicated that one of its sugar-conjugated metabolites, morphine-6-glucuronide, exerts a higher analgesic effect than its parent drug. Considering that nalbuphine is a morphine analog that follows a similar metabolic scheme, nalbuphine glucuronides were synthesized in this study and their potential analgesic effects were assessed. Nalbuphine-3-glucuronide (N3G) and nalbuphine-6-glucuronide (N6G) were synthesized based on Schmidt’s glycosylation with OPiv protections on the glycosyl donor. In a pharmacodynamic study, paw pressure and cold-ethanol tail-flick tests were conducted in rats to evaluate the analgesic response after intracisternal and i.p. administrations of nalbuphine, N3G, or N6G. The antinociceptive response was evaluated for each compound by calculating the area under the curve and the duration spent at greater than 50% maximum possible analgesia. In conclusion, intracisternal administration of N6G exhibited a stronger analgesic response than nalbuphine in the pain tests after both cold and mech. stimuli, but N3G had no obvious effect. Similar to that of morphine, the glucuronide metabolite of nalbuphine at the 6-O-position exerted at least three-fold higher antinociceptive potency and five-fold longer analgesic duration than nalbuphine. In the experiment, the researchers used (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3Related Products of 21085-72-3)

(2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3) may be used for the synthesis of HMR1098-S-Glucuronide Methyl Ester, a new K-ATP-blocking agent being developed as a drug for prevention of sudden cardiac death.Related Products of 21085-72-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Anisotropic Poisson Effect and Deformation-Induced Fluorescence Change of Elastic 9,10-Dibromoanthracene Single Crystals》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Hayashi, Shotaro; Ishiwari, Fumitaka; Fukushima, Takanori; Mikage, Shohei; Imamura, Yutaka; Tashiro, Motomichi; Katouda, Michio. Application of 523-27-3 The article mentions the following:

Elastic organic crystals have attracted considerable attention as next-generation flexible smart materials. However, the detailed information on both mol. packing change and macroscopic mech. crystal deformations upon applied stress is still insufficient. Herein, we report that fluorescent single crystals of 9,10-dibromoanthracene are elastically bendable and stretchable, which allows a detailed investigation of the deformation behavior. We clearly observed a Poisson effect for the crystal, where the short axes (b and c-axes) of the crystal are contracted upon elongation along the long axis (a-axis). Moreover, we found that the Poisson’s ratios along the b-axis and c-axis are largely different. Theor. mol. simulation suggests that the tilting motion of the anthracene may be responsible for the large deformation along the c-axis. Spatially resolved photoluminescence (PL) measurement of the bent elastic crystals reveals that the PL spectra at the outer (elongated), central (neutral), and inner (contracted) sides are different from each other. The experimental process involved the reaction of 9,10-Dibromoanthracene(cas: 523-27-3Application of 523-27-3)

9,10-Dibromoanthracene(cas: 523-27-3) can be sublimated and oxidized to generate anthraquinone. Soluble in hot benzene and hot toluene, slightly soluble in alcohol, ether and cold benzene, insoluble in water.Application of 523-27-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Design, synthesis and biological evaluation of novel hybrids of N-aryl pyrrothine-base α-pyrone as bacterial RNA polymerase inhibitors》 was published in Bioorganic & Medicinal Chemistry Letters in 2020. These research results belong to Tan, Xiangduan; Huang, Mohan; Nian, Siyun; Peng, Yanfen; Qin, Jianli; Kong, Bo; Duan, Xiaoqun. Category: bromides-buliding-blocks The article mentions the following:

Antibiotic resistance in bacteria has been an emerging public health problem, thus discovery of novel and effective antibiotics is urgent. A series of novel hybrids of N-aryl pyrrothine-base α-pyrone hybrids was designed, synthesized and evaluated as bacterial RNA polymerase (RNAP) inhibitors. Among them, compound I exhibited potent antibacterial activity against antibiotic-resistant S. aureus with the min. inhibitory concentration (MIC) in the range of 1-4μg/mL. Moreover, compound I exhibited strong inhibitory activity against E. coli RNAP with an IC50 value of 16.06μM, and cytotoxicity in HepG2 cells with IC50 value of 7.04μM. The mol. docking study further suggested that compound I binds to the switch region of bacterial RNAP. In summary, compound I is a novel bacterial RNAP inhibitor, and a promising lead compound for further optimization. In the part of experimental materials, we found many familiar compounds, such as Ethyl 5-bromovalerate(cas: 14660-52-7Category: bromides-buliding-blocks)

Ethyl 5-bromovalerate(cas: 14660-52-7) belongs to bromides. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Starazo triple switches – synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes》 was published in Beilstein Journal of Organic Chemistry in 2020. These research results belong to Heindl, Andreas H.; Wegner, Hermann A.. Synthetic Route of C6H5Br2N The article mentions the following:

Unsym. 1,3,5-tris(arylazo)benzenes – ‘starazos’ – which merge three photoswitches on one benzene ring, were successfully prepared Two different synthetic strategies, one based on Baeyer-Mills reactions and the other based on Pd-catalyzed coupling reactions of arylhydrazides and aryl halides, followed by oxidation, were investigated. The Pd-catalyzed route efficiently led to the target compounds, unsym. tris(arylazo)benzenes. These triple switches were preliminarily characterized in terms of their isomerization behavior using UV-vis and 1H-NMR spectroscopy. The efficient synthesis of this new class of unsym. tris(arylazo)benzenes opened new avenues to novel multistate switching materials. The experimental part of the paper was very detailed, including the reaction process of 3,5-Dibromoaniline(cas: 626-40-4Synthetic Route of C6H5Br2N)

3,5-Dibromoaniline(cas: 626-40-4) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Synthetic Route of C6H5Br2N

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Synthesis of All-Carbon Quaternary Centers by Palladium-Catalyzed Olefin Dicarbofunctionalization》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Koy, Maximilian; Bellotti, Peter; Katzenburg, Felix; Daniliuc, Constantin G.; Glorius, Frank. Reference of Methyltriphenylphosphonium bromide The article mentions the following:

The redox-neutral dicarbofunctionalization of tri- and tetrasubstituted olefins to form a variety of (hetero)cyclic compounds under photoinduced palladium catalysis is described. This cascade reaction process was used to couple styrenes or acryl amides with a broad range of highly decorated olefins tethered to aryl or alkyl bromides (>50 examples). This procedure enables one or two contiguous all-carbon quaternary centers to be formed in a single step. The products could be readily diversified and applied in the synthesis of a bioactive oxindole analog. The experimental part of the paper was very detailed, including the reaction process of Methyltriphenylphosphonium bromide(cas: 1779-49-3Reference of Methyltriphenylphosphonium bromide)

Methyltriphenylphosphonium bromide(cas: 1779-49-3) is used for methylenation through the Wittig reaction. It is utilized in the synthesis of an enyne and 9-isopropenyl -phenanthrene by using sodium amide as reagent. Reference of Methyltriphenylphosphonium bromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Approaching the Integer-Charge Transfer Regime in Molecularly Doped Oligothiophenes by Efficient Decarboxylative Cross-Coupling》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Liu, Jiang Tian; Hase, Hannes; Taylor, Sarah; Salzmann, Ingo; Forgione, Pat. Synthetic Route of C4H2Br2S The article mentions the following:

A library of sym. linear oligothiophene was prepared employing decarboxylative cross-coupling reaction as the key transformation. Thiophene potassium carboxylate salts were used as cross-coupling partners without the need of co-catalyst, base, or additives. This method demonstrates complete chemoselectivity and is a comprehensive greener approach compared to the existing methods. The modularity of this approach is demonstrated with the preparation of discreet oligothiophenes with up to 10 thiophene repeat units. Sym. oligothiophenes are prototypical organic semiconductors where their mol. elec. doping as a function of the chain length can be assessed spectroscopically. An oligothiophene critical length for integer charge transfer is 10 thiophene units, highlighting the potential use of discrete oligothiophenes as doped conduction or injection layers in organic electronics applications. The results came from multiple reactions, including the reaction of 2,5-Dibromothiophene(cas: 3141-27-3Synthetic Route of C4H2Br2S)

2,5-Dibromothiophene(cas: 3141-27-3) , is mainly used as pharmaceutical intermediate and synthesis intermediate. 2,5-Dibromothiophene may be used in the preparation of soluble α,ω-diformyl-a-oligothiophenes.Synthetic Route of C4H2Br2S

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Copper-Catalyzed Asymmetric Radical 1,2-Carboalkynylation of Alkenes with Alkyl Halides and Terminal Alkynes》 was published in Journal of the American Chemical Society in 2020. These research results belong to Dong, Xiao-Yang; Cheng, Jiang-Tao; Zhang, Yu-Feng; Li, Zhong-Liang; Zhan, Tian-Ya; Chen, Ji-Jun; Wang, Fu-Li; Yang, Ning-Yuan; Ye, Liu; Gu, Qiang-Shuai; Liu, Xin-Yuan. SDS of cas: 2635-13-4 The article mentions the following:

A copper-catalyzed intermol. three-component asym. radical 1,2-carboalkynylation of alkenes has been developed, providing straightforward access to diverse chiral alkynes from readily available alkyl halides and terminal alkynes. The utilization of a cinchona alkaloid-derived multidentate N,N,P-ligand is crucial for the efficient radical generation from mildly oxidative precursors by copper and the effective inhibition of the undesired Glaser coupling side reaction. The substrate scope is broad, covering (hetero)aryl-, alkynyl-, and aminocarbonyl-substituted alkenes, (hetero)aryl and alkyl as well as silyl alkynes, and tertiary to primary alkyl radical precursors with excellent functional group compatibility. Facile transformations of the obtained chiral alkynes have also been demonstrated, highlighting the excellent complementarity of this protocol to direct 1,2-dicarbofunctionalization reactions with C(sp2/sp3)-based reagents. In the experiment, the researchers used many compounds, for example, 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4SDS of cas: 2635-13-4)

Furthermore, the coupling of 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4) with β-methallyl alcohol was catalyzed by Pd(OAc)2 in combination with P(t-Bu)3.SDS of cas: 2635-13-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Design of a Kilogram Scale, Plug Flow Photoreactor Enabled by High Power LEDs》 was published in Organic Process Research & Development in 2020. These research results belong to Levesque, Francois; Di Maso, Michael J.; Narsimhan, Karthik; Wismer, Michael K.; Naber, John R.. Quality Control of 1-Bromo-4-(trifluoromethyl)benzene The article mentions the following:

A simple and inexpensive photoreactor with a throughput of kilograms of material per day has been developed. This achievement was enabled by using high-power Light Emitting Diodes (LEDs) to provide high light d., leading to minimization of the footprint of the reactor. A study of the impact of tube diameter enabled maximization of the photon absorbance without increasing photocatalyst loading. Further optimization of reaction conditions using a design of experiments (DoE) elucidated reaction sensitivities that allowed the reaction rate, yield, and productivity to be maximized upon scale-up. The reactor has been operated continuously for 6 h leading to reaction performance that provided 12 kg of material per day at 90% conversion. The experimental process involved the reaction of 1-Bromo-4-(trifluoromethyl)benzene(cas: 402-43-7Quality Control of 1-Bromo-4-(trifluoromethyl)benzene)

1-Bromo-4-(trifluoromethyl)benzene(cas: 402-43-7) 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. Quality Control of 1-Bromo-4-(trifluoromethyl)benzene Alkyl bromides are mainly used as alkylating agents and also find application as a solvent to extract oil from seeds and wool.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties》 was written by Altinolcek, Nuray; Battal, Ahmet; Tavasli, Mustafa; Peveler, William J.; Yu, Holly A.; Skabara, Peter J.. Name: 3,6-Dibromo-9H-carbazole And the article was included in Beilstein Journal of Organic Chemistry in 2020. The article conveys some information:

Two novel carbazole-based compounds I [R = 4-formyl, 5-formyl] were synthesized as potential candidates for application in organic electronics. The materials were fully characterised by NMR spectroscopy, mass spectrometry, FTIR, thermogravimetric anal., differential scanning calorimetry, cyclic voltammetry, and absorption and emission spectroscopy. Compounds I, both of which were amorphous solids, were stable up to 291°C and 307°C, resp. Compounds I showed three distinctive absorption bands: high and mid energy bands due to locally excited (LE) transitions and low energy bands due to intramol. charge transfer (ICT) transitions. In dichloromethane solutions compounds I gave emission maxima at 561 nm and 482 nm with quantum efficiencies of 5.4% and 97.4% ± 10%, resp. At pos. potential, compounds I gave two different oxidation peaks, resp.: quasi-reversible at 0.55 V and 0.71 V, and reversible at 0.84 V and 0.99 V. At neg. potentials, compounds I only exhibited an irreversible reduction peak at -1.86 V and -1.93 V, resp. The experimental process involved the reaction of 3,6-Dibromo-9H-carbazole(cas: 6825-20-3Name: 3,6-Dibromo-9H-carbazole)

3,6-Dibromo-9H-carbazole(cas: 6825-20-3) is used as a pharmaceutical intermediate, and also an important intermediate of synthesizing optoelectronic materials. It has been used as a reagent in the synthesis of P7C3-A20 which is a potent neuroprotective agent.Name: 3,6-Dibromo-9H-carbazole

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tian, Duanshuai; Xu, Ronghua; Zhu, Jinbin; Huang, Jianxun; Dong, Wei; Claverie, Jerome; Tang, Wenjun published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Asymmetric Hydroesterification of Diarylmethyl Carbinols》.Reference of 5-Bromobenzo[d][1,3]dioxole The article contains the following contents:

An efficient asym. hydroesterfication of diarylmethyl carbinols is developed for the first time with a Pd-WingPhos catalyst, resulting in a series of chiral 4-aryl-3,4-dihydrocoumarins in excellent enantioselectivities and good yields. The method features mild reaction conditions, a broad substrate scope, use of easily accessible starting materials, and low palladium loadings. A plausible stereochem. model is also proposed with the Pd-WingPhos catalyst. This method has enabled a 4-step asym. synthesis of (R)-tolterodine from readily available starting materials. In the experiment, the researchers used 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4Reference of 5-Bromobenzo[d][1,3]dioxole)

Furthermore, the coupling of 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4) with β-methallyl alcohol was catalyzed by Pd(OAc)2 in combination with P(t-Bu)3.Reference of 5-Bromobenzo[d][1,3]dioxole

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary