Tag: M.W=200-250

Percec, Virgil published the artcileSelf-organization of rectangular bipyramidal helical columns by supramolecular orientational memory epitaxially nucleated from a Frank-Kasper σ phase, Recommanded Product: 1-Bromododecane, the publication is Giant (2022), 100084, database is CAplus.

Programming living and soft complex matter via primary structure and self-organization represents the key methodol. employed to design functions in biol. and synthetic nanoscience. Memory effects have been used to create com. technologies including liquid crystal displays and biomedical applications based on shape memory polymers. Supramol. orientational memory (SOM), induced by an epitaxial nucleation mediated by the close contact spheres of cubic phases, emerged as a pathway to engineer complex nanoscale soft matter of helical columnar hexagonal arrays. SOM preserves the crystallog. directions of close contact supramol. spheres from the 3D phase upon cooling to the columnar hexagonal periodic array. Despite the diversity of 3D periodic and quasiperiodic nanoarrays of supramol. dendrimers, including Frank-Kasper and quasicrystal, all examples of SOM to date were mediated by Im3m (body-centered cubic, BCC) and Pm3n (Frank-Kasper A15) cubic phases. Expanding the scope of SOM to non-cubic arrays is expected to generate addnl. morphologies that were not yet available by any other methods. Here we demonstrate the SOM of a dendronized triphenylene that self-organizes into helical columnar hexagonal and tetragonal P4₂/mnm (Frank-Kasper σ) phases. Structural anal. of oriented fibers by X-ray diffraction reveals that helical columnar hexagonal domains self-organize an unusual rectangular bipyramidal morphol. upon cooling from the σ phase. The discovery of SOM in a non-cubic Frank-Kasper phase indicates that this methodol. may be expanded to other periodic and quasiperiodic nanoarrays organized from self-assembling dendrimers and, most probably, to other soft and living complex matter.

Giant published new progress about 143-15-7. 143-15-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromododecane, and the molecular formula is C12H25Br, Recommanded Product: 1-Bromododecane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Fuchigami, Takeshi published the artcileSynthesis and Characterization of 9-(4-[¹⁸F]Fluoro-3-(hydroxymethyl)butyl)-2-(phenylthio)-6-oxopurine as a Novel PET Agent for Mutant Herpes Simplex Virus Type 1 Thymidine Kinase Reporter Gene Imaging, Name: 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, the publication is Molecular Imaging and Biology (2020), 22(5), 1151-1160, database is CAplus and MEDLINE.

Purpose: [¹⁸F]FHBG has been used as a positron emission tomog. (PET) imaging tracer for the monitoring of herpes simplex virus type 1 thymidine kinase (HSV1-tk), a reporter gene for cell and gene therapy in humans. However, this tracer shows inadequate blood-brain barrier (BBB) penetration and, therefore, would be limited for accurate quantification of reporter gene expression in the brain. Here, we report the synthesis and evaluation of 9-(4-[¹⁸F]fluoro-3-(hydroxymethyl)butyl)-2(phenylthio)-6-oxopurine ([18F]FHBT) as a new PET tracer for imaging reporter gene expression of HSV1-tk and its mutant HSV1-sr39tk, with the aim of improved BBB penetration. Procedures: [¹⁸F]FHBT was prepared by using a tosylate precursor and [18F]KF. The cellular uptake of [¹⁸F]FHBT was performed in HSV1-sr39tk-pos. (+) or HSV1-sr39tk-neg. (-) MDA-MB-231 breast cancer cells. The specificity of [¹⁸F]FHBT to assess HSV1-sr39tk expression was evaluated by in vitro blocking studies using 1 mM of ganciclovir (GCV). Penetration of [¹⁸F]FHBT and [¹⁸F]FHBG across the BBB was assessed by dynamic PET imaging studies in normal mice. Results: The tosylate precursor reacted with [¹⁸F]KF using Kryptofix2.2.2 followed by deprotection to give [¹⁸F]FHBT in 10 % radiochem. yield (decay-corrected). The uptake of [¹⁸F]FHBT in HSV1-sr39tk (+) cells was significantly higher than that of HSV1-sr39tk (-) cells. In the presence of GCV (1 mM), the uptake of [¹⁸F]FHBT was significantly decreased, indicating that [¹⁸F]FHBT serves as a selective substrate of HSV1-sr39TK. PET images and time-activity curves of [¹⁸F]FHBT in the brain regions showed similar initial brain uptakes (∼12.75 min) as [¹⁸F]FHBG (P > 0.855). Slower washout of [¹⁸F]FHBT was observed at the later time points (17.75 – 57.75 min, P > 0.207). Conclusions: Although [¹⁸F]FHBT showed no statistically significant improvement of BBB permeability compared with [¹⁸F]FHBG, we have demonstrated that the 2-(phenylthio)-6-oxopurine backbone can serve as a novel scaffold for developing HSV1-tk/HSV1-sr39tk reporter gene imaging agents for addnl. research in the future.

Molecular Imaging and Biology published new progress about 97845-58-4. 97845-58-4 belongs to bromides-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Bromide, name is 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane, and the molecular formula is C8H15BrO2, Name: 5-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Sui, Jingzhi published the artcileSynthesis of Trans-4a,12b/3,4-Dihydrodibenzo[f,h]quinolin-2(1H)-Ones and Dibenzo[f,h]quinolin-2(1H)-Ones via Irradiation of 6-Biphenylpyridine-2(1H)-Ones, Product Details of C7H8BBrO3, the publication is Advanced Synthesis & Catalysis (2021), 363(14), 3554-3559, database is CAplus.

The synthesis of trans-4a,12b-dihydrodibenzo[f,h]quinolin-2(1H)-ones, dibenzo[f,h]quinolin-2(1H)-ones and 3,4-dihydrodibenzo[f,h]quinolin-2(1H)-ones via photo-induced annulation of 6-([1,1′-biphenyl]-2-yl)pyridine-2(1H)-ones under irradiation of a 313 nm UV light was described. Trans-4a,12b-dihydrodibenzo[f,h]quinolin-2(1H)-ones were obtained in 82-95% yields when the irradiation time was 3 h. Dibenzo[f,h]quinolin-2(1H)-ones were obtained by irradiating biphenylpyridinones for 12 h in the presence of iodine. Heating the solution of trans-4a,12b-dihydrodibenzo[f,h]quinolin-2(1H)-ones in DMF at 130°C for 24 h gave 3,4-dihydrodibenzo[f,h]quinolin-2(1H)-ones via a double 1,3-H shift. The demonstrated protocols showed the diversity of photo-induced cyclization of biphenylpyridinones.

Advanced Synthesis & Catalysis published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is CBF6K, Product Details of C7H8BBrO3.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Stensrud, Kenneth F. published the artcileFluorinated photoremovable protecting groups: the influence of fluoro substituents on the photo-Favorskii rearrangement, Synthetic Route of 1998-61-4, the publication is Photochemical & Photobiological Sciences (2008), 7(5), 614-624, database is CAplus and MEDLINE.

To further explore the nature of the photo-Favorskii rearrangement and its commitment to substrate photorelease from p-hydroxyphenacyl (pHP), an array of ten new fluorinated pHP γ-aminobutyric acid (GABA) derivatives was synthesized and photolyzed. The effects of fluorine substitution on the chromophore and the photophys. and photochem. properties of these new chromophores were shown to be derived primarily from the changes in the ground state pK_a of the phenolic groups. The quantum yields and rate constants for release are clustered around Φ_dis = 0.20 ± 0.05 and k_r = 8 ± 7 × 10⁷ s^-1 (H₂O), resp. The triplet lifetimes of the pHP GABA derivatives were concentrated in the range of 0.4-6.0 ns (H₂O). The corresponding deprotonated conjugate bases displayed reduced efficiencies by 50% or more (one exception) and exhibited a weak fluorescence in pH 8.2 buffer. Pump-probe spectroscopy studies have further defined the rates of intersystem crossing and the lifetimes of the reactive triplet state of the fluoro pHP chromophore.

Photochemical & Photobiological Sciences published new progress about 1998-61-4. 1998-61-4 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzene,Phenol, name is 4-Bromo-2,3,5,6-tetrafluorophenol, and the molecular formula is C20H12N2O2, Synthetic Route of 1998-61-4.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Rutjes, Floris P. J. T. published the artcileCyclic 1,2-dinitrogen compounds through N,N’-bis(methoxycarbonyl)hydrazinium intermediates, Product Details of C7H13BrSi, the publication is Tetrahedron Letters (1988), 29(52), 6975-8, database is CAplus.

Acid-catalyzed cyclization of methoxymethyl-substituted acyclic hydrazides provides cyclic hydrazides in moderate to good yields. E.g., MeOCH₂[N(CO₂Me)]₂(CH₂)_nCH:CH₂ (n = 1-3) were treated with TiCl₄ in CH₂Cl₂ to give 32, 80, and 15% cyclic hydrazides I (same n), resp. A mechanism involving bis(methoxycarbonyl)hydrazinium intermediates is presented.

Tetrahedron Letters published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C7H13BrSi, Product Details of C7H13BrSi.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Mukai, Chisato published the artcileRh(I)-catalyzed allenic Pauson-Khand reaction: first construction of the bicyclo[6.3.0]undecadienone ring system, Category: bromides-buliding-blocks, the publication is Tetrahedron (2005), 61(46), 10983-10994, database is CAplus.

The Rh(I)-catalyzed Pauson-Khand reaction of allenynes afforded the bicyclo[6.3.0]undecadienones as well as their benzo and furo derivatives E.g., [RhCl(CO)₂]₂ catalyzed the Pauson-Khand reaction of CH₂:C:C(SO₂Ph)CH₂C(CO₂Me)₂(CH₂)₃CCPh to give 43% bicyclo[6.3.0] compound I. In addition, a novel [RhCl(CO)₂]₂-catalyzed [2,3]-sigmatropic rearrangement of the sulfinic ester species of propargyl alcs. was developed. E.g., [RhCl(CO)₂]₂ catalyzed the [2,3]-sigmatropic rearrangement of PhCCCH₂OSOPh to give 63% PhSO₂CPh:C:CH₂.

Tetrahedron published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C7H13BrSi, Category: bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Arbuzov, B. A. published the artcileAction of triethyl phosphite and diethyl sodium phosphite on some dihalo derivatives, Application In Synthesis of 594-81-0, the publication is Zhurnal Obshchei Khimii (1951), 99-107, database is CAplus.

To (EtO)₂PONa (from 44.2 g. ester and 7.2 g. Na) in 450 ml. dry Et₂O was added 28.5 g. ClCH₂CH₂CN, b₁₀ 63-5°, n²⁰_D 1.4370, d²⁰₂₀ 1.1461, over 0.5 hr.; after refluxing 1 hr., the filtrate yielded 42.7 g. (70.2%) (EtO)₂P(O)CH₂CH₂CN, b₇ 150-2°, b₂ 127-8°, n²⁰_D 1.4380, d²⁰₂₀ 1.1127; this (9.9 g.) heated 8 hrs. to 115-30° in a sealed tube with 30 ml. 2:1 HCl and evaporated gave 6.2 g. (78.5%) (HO)₂P(O)CH₂CH₂CO₂H, m. 166° (by Soxhlet extraction with dry C₆H₆, then with dry Me₂CO). Addition of 40.6 g. BrCH₂CHBrCN, b₁₀ 89-90°, n²⁰_D 1.5390, d²⁰₂₀ 2.0955, to (EtO)₂PONa (from 53.3 g. ester and 8.7 g. Na) in 500 ml. Et₂O and treatment as above gave after repeated fractionation 7 g. (11.9%) (EtO)₂POH, b₇ 60-5°, n²⁰_D 1.4080, d²⁰₂₀ 1.0667, and 9.5 g. (26.4%) (EtO)₂P(O)C(CN):CH₂ or (EtO)₂P(O)CH:CHCN, b₁ 124-7°, n²⁰_D 1.4360, d²⁰₂₀ 1.1277, soluble in H₂O and reacting rapidly with Br water or KMnO₄; hydrolysis with 1:1 HCl 10 hrs. at 150-65° gave on evaporation a mixture of products, which, on removal of NH₄Cl by addition of dry EtOH and evaporation of the extract, gave 4 g. oil; this with BaCO₃ gave a mixture of Ba salts, from which was isolated a H₂O-insoluble Ba salt, possibly C₆H₄P₂O₁₁Ba₃, BaHPO₄, or Ba phosphonoacrylate; a considerable amount of H₂O-soluble C₆H₈O₁₀P₂Ba was also isolated. The products were not identified further. Addition of 32.8 g. (EtO)₃P to 20.2 g. BrCH₂CHBrCN over 0.5 hr. led to a temperature rise to 87°, where it was kept for removal of the EtBr; after 15 min. at 150°, the mixture yielded a total of 19 g. EtBr, but distillation of the residue failed to yield definite products. Addition of 16.1 g. PhCH:CHBr, b₁₀ 88-90°, n²⁰_D 1.6018, d²⁰₂₀ 1.4094, to (EtO)₂PONa (from 13.1 g. ester and 2 g. Na) in 100 ml. MePh (in Et₂O the reaction does not occur) gave no immediate NaBr, but after a 4-hr. reflux 6.6 g. NaBr precipitated and fractionation of the solution gave 7.1 g. (44%) original bromide and 1.9 g. (12%) PhCH(PO₃Et₂)CH₂P(O)(OEt)₂, b₁ 181°, n²⁰_D 1.4920, d²⁰₂₀ 1.1524, which on hydrolysis 7 hrs. at 120-30° with 1:1 HCl gave the free diphosphonic acid, m. 212-14° (from H₂O). Possibly, both phosphono groups are attached to the terminal C atom, but no further characterization was attempted. PhCH:CHBr (14.9 g.) added to 14.5 g. (EtO)₃P at 200-10° did not react and practically all the (EtO)₃P was recovered; heating the components 8 hrs. to 180-200° in a sealed tube gave only traces of high-boiling products. Addition of 34.6 g. PhCHBrCH₂Br in Et₂O over 35 min. to (EtO)₂PONa (from 37.5 g. ester and 6 g. Na) in 500 ml. Et₂O, gave a precipitate of NaBr and, after refluxing 2 hrs., 6.3 g. (53.7%) styrene, about 12 g. (EtO)₂POH, 4.8 g. unreacted dibromide, and about 14 g. of a fraction b₁₁ 90-132°, which on redistillation gave a liquid, b₃ 105-130°; this with 2-C₁₀H₇NH₂ gave 1.2 g. (EtO)₂P(O)NHC₁₀H₇-2, m. 69°, which indicated that the high-boiling liquid was probably (EtO)₂POP(O)(OEt)₂ (cf. Arbuzov and Arbuzov, C.A. 25, 3618). Addition of 22 g. (EtO)₃P over 1 hr. to 16 g. PhCHBrCH₂Br preheated to 155-60° and heating 1 hr. to 165-70° gave 8.6 g. EtBr, 4.7 g. (50.2%) styrene, 3.8 g. crude (EtO)₂POH, b₁₁ 69-72°, 1.7 g. unreacted dibromide, and 10.3 g. crude liquid, b₂ 103-57°, which on redistillation gave a product, b₂ 117-31°, forming with 2-C₁₀H₇NH₂, 0.8 g. (EtO)₂P(O)NHC₁₀H₇, corresponding to a 4.8% yield of tetra-Et subphosphate. When PhCHBrCH₂Br is heated alone to 155-70°, much HBr forms, thus explaining the formation of (EtO)₂POH above. Heating 9.2 g. dibromide to 195-205°, gradual addition of 10.2 g. (EtO)₂POH, and heating 1 hr. to 210-15° gave 4.1 g. EtBr and about 1.5 g. styrene (crude). Addition of 21.4 g. PhCMe:CHBr, b₁₁ 103-5°, n²⁰_D 1.5880, d²⁰₂₀ 1.3790, to (EtO)₂PONa (from 16 g. ester and 2.5 g. Na) in 200 ml. Et₂O and refluxing 1 hr. gave 2.1 g. unreacted bromide and 4 g. (16%) PhCMe:CHP(O)(OEt)₂, b₁ 146-9°, n²⁰_D 1.5210, d²⁰₂₀ 1.1094, which immediately reacts with Br; hydrolysis by 1:1 HCl 6 hrs. at 135-45° in a sealed tube and evaporation gave some crude PhCMe:CH₂ and H₃PO₄, isolated as the PhNHNH₂ salt, m. 155° (from EtOH). Addition over 40 min. of 12.5 g. (EtO)₃P to 13.6 g. PhCMe:CHBr preheated to 150-60° and heating 1 hr. to 165-70° gave 2.3 g. EtBr, 2.1 g. unreacted bromide, 3.1 g. (EtO)₂POH, and 5 g. (33.5%) PhCMe:CHP(O)(OEt)₂, b_1.5 149-50°, n²⁰_D 1.5190, d²⁰₂₀ 1.1009, which on hydrolysis with 1:1 HCl at 120-30° cleaves into H₃PO₄ and PhCMe:CH₂. PhCMeBrCH₂Br (30.6 g.) with (EtO)₂PONa (from 33 g. ester and 5.3 g. Na) in 400 ml. Et₂O, refluxed 2 hrs., gave 5.9 g. (45.4%) PhCMe:CH₂ and apparently about 6 g. (EtO)₂POH; no individual substances of higher b.p. were identified. (EtO)₂PONa with (Me₂CBr)₂ yields apparently tetra-Et subphosphate and Me₂C:CMe₂.

Zhurnal Obshchei Khimii published new progress about 594-81-0. 594-81-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 2,3-Dibromo-2,3-dimethylbutane, and the molecular formula is C6H12Br2, Application In Synthesis of 594-81-0.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Durka, Krzysztof published the artcileThe Influence of Boronate Groups on the Selectivity of the Br-Li Exchange in Model Dibromoaryl Boronates, Product Details of C7H8BBrO2, the publication is European Journal of Organic Chemistry (2013), 2013(15), 3023-3032, database is CAplus.

The selectivity of the Br/Li exchange reaction of 6-butyl-2-(2,5-dibromophenyl)-1,3,6,2-dioxazaborocane (2,5-Br₂C₆H₃B(OCH₂CH₂)₂NBu) and the analogous anionic derivatives, 2,5-Br₂C₆H₃B(OiPr)₃Li and 2,5-Br₂C₆H₃BF₃K, was studied using BuLi as the lithiating reagent. In the case of the former compound there was a slight preference for lithiation at the 5-position. For 2,5-Br₂C₆H₃B(OiPr)₃Li, the lithiation occurred exclusively at C5, but for 2,5-Br₂C₆H₃BF₃K, 2-lithiation was preferred. Calculations performed for the lithiation of ortho- and meta-brominated Ph boronates revealed that ortho-lithiated aryl boronates are thermodynamically more stable, but that the Br/Li exchange is generally dictated by kinetics, which accounts for the variation of selectivity depending on the type of boronate group. The successful generation of the 2,5-dilithiophenyl boronate species 2,5-Li₂C₆H₃B(OCH₂CH₂)₂NBu by a double Br/Li interconversion is reported. The Br/Li exchange in the related 6-butyl-2-[3-(2,5-dibromothienyl)]-1,3,6,2-dioxazaborocane, 2,5-Br₂-3-ThB(OCH₂CH₂)₂NBu, occurred preferentially at the 5-position, but the product was readily transformed into the more stable 2-lithiated isomer. The use of 2 equiv of BuLi resulted in the efficient formation of the dilithiated species, 2,5-Li₂-3-ThB(OCH₂CH₂)₂NBu. The obtained lithiated aryl boronates were converted into functionalized arylboronic acids by treatment with selected electrophiles.

European Journal of Organic Chemistry published new progress about 1450711-53-1. 1450711-53-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester, name is (2-Bromo-5-methylphenyl)boronic acid, and the molecular formula is C7H8BBrO2, Product Details of C7H8BBrO2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Kurach, Pawel published the artcileOne-pot generation of lithium (lithiophenyl)trialkoxyborates from substituted dihalobenzenes (Hal = Br, I) and their derivatization with electrophiles, Synthetic Route of 849062-12-0, the publication is European Journal of Organic Chemistry (2008), 3171-3178, database is CAplus.

The simple one-pot approach to synthetically useful phenyl-trialkoxyborates bearing lithium at the Ph ring has been developed starting with 1,3- and 1,4-diiodobenzene, as well as several activated dibromobenzenes and bromoiodo-benzenes. The general sequence of transformations involves halogen-lithium exchange by using nBuLi and subsequent boronation with a trialkylborate. The resulting lithium (halophenyl)trialkoxyborates were then subjected to halogen-lithium exchange in situ with a second equivalent of nBuLi to give dianionic lithium (lithiophenyl)trialkoxyborates. Treatment with selected electrophiles afforded substituted arylboronic acids and/or their pinacol esters as final products in moderate-to-good yields.

European Journal of Organic Chemistry published new progress about 849062-12-0. 849062-12-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Bromo-5-methoxyphenyl)boronic acid, and the molecular formula is C7H8BBrO3, Synthetic Route of 849062-12-0.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Chen, Wen-Bin published the artcileSynthesis and screening of novel inositol phosphonate derivatives for anticancer functions in vitro, Synthetic Route of 66197-72-6, the publication is Chinese Chemical Letters (2015), 26(3), 329-333, database is CAplus.

Phosphonates have been frequently used as suitable isosteric and isoelectronic replacements for biol. important phosphates in the development of drugs or drug candidates because of their stability toward the action of phosphatases and other enzymes. In this paper, 12 mono-phosphonate inositol compounds, e.g. I, were prepared with phosphonate instead of phosphate by two kinds of strategies, nucleophilic substitution and Arbuzov rearrangement, resp. All compounds were evaluated in vitro for their activity against non-small cell lung cancer (NSCLC) cell line A549. I exhibited good antitumor activity at 10 μg/mL.

Chinese Chemical Letters published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, Synthetic Route of 66197-72-6.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary