Month: April 2022

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Bromomethyl-1,3-dioxolane(SMILESS: BrCC1OCCO1,cas:4360-63-8) is researched.Category: chiral-oxygen-ligands. The article 《Modular Synthesis of Bicyclic and Tricyclic (Aza-) Arenes from Nucleophilic (Aza-)Arenes with Electrophilic Side Arms via [4+2] Annulation Reactions》 in relation to this compound, is published in Advanced Synthesis & Catalysis. Let’s take a look at the latest research on this compound (cas:4360-63-8).

An efficient strategy for the synthesis of bicyclic aza-arenes I [R1 = Me, Ph, 2-thienyl, etc.; R2 = Me, OEt, OBn, etc.; Ar = OMe, Cl, Ph, etc.] and tricyclic aza-arenes, e.g., II from a nucleophilic aza-arene with an electrophilic side arm was developed. The aza-arene precursor had both nucleophilic and electrophilic sites, which were fixed at a 1,4-distance. The bicyclic and tricyclic (aza-)arene products I and II were constructed via [4+2] annulation by using scandium(III) triflate as a catalyst and enolizable ketones or aldehydes as the counterpart reagents. A variety of six-membered carbocycles and heterocycles, such as indolizines, indoles, naphthalenes, carbazoles and pyrido[1,2-α]indoles, were successfully synthesized. Some one-pot sequential reactions were also developed, in which the 1,4-donor-acceptor precursors can be synthesized via oxidation of alcs. or a proper condensation reaction.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Related Products of 707-61-9. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Phospho sugars; novel preparation and their glycosyl compounds. Author is Ikai, Koichi; Iida, Akihito; Yamashita, Mitsuji.

Treatment of 1-phenyl-2-, and -3-phospholene 1-oxides with NBS affords 4-bromo-1-phenyl-2-phospholene 1-oxide (I). Substitution of the bromide with acetate, followed by stereoselective oxidation with osmium tetroxide and peracetylation with acetic anhydride/pyridine affords phospho sugar derivatives II of tetrafuranose. Furthermore, glycosyl compounds III (R = iodo, OAc, SCN, N3) of phospho sugars were prepared from 3-methyl-1-phenyl-2-phospholene 1-oxide by bromination and nucleophilic substitution reactions.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《2- and 5-Fluoronicotinic acids》. Authors are Beaty, R. D.; Musgrave, W. K. R..The article about the compound:Methyl 5-fluoro-3-pyridinecarboxylatecas:455-70-9,SMILESS:COC(=O)C1=CC(F)=CN=C1).Name: Methyl 5-fluoro-3-pyridinecarboxylate. Through the article, more information about this compound (cas:455-70-9) is conveyed.

5-Aminonicotinic acid (I) (3 g.) in 20 cc. 40% HBF4 at -5° treated with 2.5 g. NaNO2, the mixture kept 1 h., heated 30 min. at 50°, neutralized with Na2CO3, and the resulting salt refluxed 2-3 h. with 3% MeOH-H2SO4, gives 0.3 g. Me 5-fluoronicotinate, m. 48°. The 2-isomer of I (2 g.) in 10 cc. 40% HBF4, diazotized with 1 g. NaNO2 in 10 cc. H2O at 0 to -5°, and the solution kept 1 h. at 0°, heated 1 h. at 50-60°, and basified to pH 5 with NaOH, gives 33% 2-fluoronicotinic acid, m. 164-5°; the Me ester m. 74-5° and the amide m. 124°. 3-Fluoropicolinic acid could not be prepared by this method.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine(SMILESS: N1(P2OC3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5O2)C7=CC=CC=C7C=CC8=CC=CC=C81,cas:1265884-98-7) is researched.Name: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole. The article 《Total Synthesis of Taiwaniadducts B, C, and D》 in relation to this compound, is published in Journal of the American Chemical Society. Let’s take a look at the latest research on this compound (cas:1265884-98-7).

The first total syntheses of taiwaniadducts B, C, and D have been accomplished. Two diterpenoid segments [trans-ozic Me ester (I) and II] were prepared with high enantiopurity, both through Ir-catalyzed asym. polyene cyclization. A sterically demanding I + II intermol. Diels-Alder reaction promoted by Er(fod)3 assembled the scaffold of taiwaniadducts B and C. A carbonyl-ene cyclization forged the cage motif of taiwaniadduct D at a late stage, providing over 200 mg of this compound

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Nija, B.; Rasheed, Arun; Kottaimuthu, A. published the article 《Development, characterization and pharmacological evaluation of amino acid prodrugs of (+)-Ibuprofen》. Keywords: Ibuprofen amino acid prodrug pharmacol evaluation.They researched the compound: H-Trp-OMe.HCl( cas:7524-52-9 ).Reference of H-Trp-OMe.HCl. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:7524-52-9) here.

The current research work investigate the neuronal pathway associated with NSAIDs that lead to the reduction in the initiation and progression of neurodegenerative diseases such as Alzheimer’s disease, Parkinsonism, etc. This research was developed amino acid prodrugs of the active enantiomer of ibuprofen, (+)-IBN and checks the pharmacol. effects, neuroprotective effect, anti inflammatory effect and anti-ulcerogenic effect. The treatment using (+)-IBN reduced the action of micoglia and the release of cytokine especially TNFα that are mainly involved in the neurodegenerative process. (+)- IBN reduced the deposition of soluble beta amyloid plaque by inhibiting the amyloid precursor protein, beta-secretase 1 and also enhancing the degradation process of beta amyloid via induction of insulin degrading enzyme. (+)-IBN also showed the property that the reduction in the TAU misfolding process. Therefore, the synthesized (+)-IBN amino acid prodrugs treatment effectively produce neuroprotective action, both restoring memory realed risk factors and reversing multiple brain neuropathol. hallmarks. The current research study developed the three amino acid prodrugs of (+)-ibuprofen by conjugating with L-Ph alanine, L-tryptophan and L-tyrosine also the physico-chem. characterization and spectral characterization was done. This study modify the carboxylic acid functional group present in the NSAIDs that lead to the formation of prodrugs with enhanced anti-inflammatory activity, reduced side effects and protective effect against neurodegenerative processes.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: H-Trp-OMe.HCl( cas:7524-52-9 ) is researched.Safety of H-Trp-OMe.HCl.Chan, Hwai-Chien; Bueno, Bianca; Le Roch, Adrien; Gagnon, Alexandre published the article 《Copper-promoted N-arylation of the imidazole side chain of protected histidine by using triarylbismuth reagents》 about this compound( cas:7524-52-9 ) in Chemistry – A European Journal. Keywords: dipeptide arylated histidine synthesis functional group; histidine imidazole arylation copper catalyst triarylbismuth reagent; arylation reaction mechanism; N-arylation; copper catalysis; histidine; imidazole; organobismuthines. Let’s learn more about this compound (cas:7524-52-9).

The N-arylation of the side chain of histidine by using triarylbismuthines is reported. The reaction is promoted by copper(II) acetate in dichloromethane at 40°C under oxygen in the presence of diisopropylethylamine and 1,10-phenanthroline and allows the transfer of aryl groups with substituents at any position of the aromatic ring. The reaction shows excellent functional group tolerance and is applicable to dipeptides where the histidine is located at the N terminus. A histidine-guided backbone N-H arylation was observed in dipeptides where the histidine occupies the C terminus.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: H-Trp-OMe.HCl(SMILESS: N[C@@H](CC1=CNC2=CC=CC=C12)C(OC)=O.[H]Cl,cas:7524-52-9) is researched.Formula: C7H14O6. The article 《Examination of sulfonamide-based inhibitors of MMP3 using the conditioned media of invasive glioma cells》 in relation to this compound, is published in Journal of Enzyme Inhibition and Medicinal Chemistry. Let’s take a look at the latest research on this compound (cas:7524-52-9).

Glioblastoma multiforme (GBM) is the deadliest and the most common primary malignant brain tumor. The median survival for patients with GBM is around one year due to the nature of glioma cells to diffusely invade that make the complete surgical resection of tumors difficult. Based upon the connexin43 (Cx43) model of glioma migration we have developed a computational framework to evaluate MMP inhibition in materials relevant to GBM. Using the ilomastat Leu-Trp backbone, we have synthesized novel sulfonamides and monitored the performance of these compounds in conditioned media expressing MMP3. From the results discussed herein we demonstrate the performance of sulfonamide based MMPIs included AP-3, AP-6, and AP-7.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Research and development of phospha sugar anti-cancer agents with anti-leukemic activity, the main research direction is phenylphospholene phospha sugar analog preparation antileukemic activity.Name: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide.

We have synthesized three deoxybromophospha sugar analogs, 4-bromo-3-methyl-1-phenyl-2-phospholene 1-oxide (MBMPP (2)), 2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide (DBMPP (3)), the 2,3,4-tribromo-3-methyl-1-phenylphospholane 1-oxide (TBMPP (4)), by the reaction of 3-methyl-1-phenyl-2-phospholene 1-oxide (1b) and/or 2 with bromine, and investigated their potentials as anti-leukemic agents against human leukemia cell lines of K562 and U937. Cells’ growth inhibition was determined by using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) in vitro assay. All agents showed inhibitory effects on leukemia cell proliferation, indicating that inhibition appeared to be dependent on number of bromine substituent in the heterocyclic structure. Further, the phospha sugar derivatives did not show any inhibitory effects on normal cell proliferation. These agents may facilitate the development of new strategies in mol. targeting anti-leukemic therapy.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: H-Trp-OMe.HCl(SMILESS: N[C@@H](CC1=CNC2=CC=CC=C12)C(OC)=O.[H]Cl,cas:7524-52-9) is researched.Safety of 5-(4-Pyridyl)-1H-tetrazole. The article 《Configurational and Constitutional Dynamics of Enamine Molecular Switches》 in relation to this compound, is published in Chemistry – A European Journal. Let’s take a look at the latest research on this compound (cas:7524-52-9).

Dual configurational and constitutional dynamics in systems based on enamine mol. switches has been systematically studied. pH-responsive moieties, such as 2-pyridyl and 2-quinolinyl units, were required on the “”stator”” part, also providing enamine stability through intramol. hydrogen-bonding (IMHB) effects. Upon protonation or deprotonation, forward and backward switching could be rapidly achieved. Extension of the stator π-system in the 2-quinolinyl derivative provided a higher E-isomeric equilibrium ratio under neutral conditions, pointing to a means to achieve quant. forward/backward isomerization processes. The “”rotor”” part of the enamine switches exhibited constitutional exchange ability with primary amines. Interestingly, considerably higher exchange rates were observed with amines containing ester groups, indicating potential stabilization of the transition state through IMHB. Acids, particularly BiIII, were found to efficiently catalyze the constitutional dynamic processes. In contrast, the enamine and the formed dynamic enamine system showed excellent stability under basic conditions. This coupled configurational and constitutional dynamics expands the scope of dynamic C-C and C-N bonds and potentiates further studies and applications in the fields of mol. machinery and systems chem.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Investigations on the isomerization of ring-substituted derivatives of 3-nitraminopyridines. I. Chloro-3-nitraminopyridines》. Authors are Czuba, Wladyslaw.The article about the compound:5-Chloropyridin-3-aminecas:22353-34-0,SMILESS:NC1=CC(=CN=C1)Cl).Synthetic Route of C5H5ClN2. Through the article, more information about this compound (cas:22353-34-0) is conveyed.

6-(m. 139°), 2- (m. 100-3°), 5- (m. 146°), and 4-Chloro-3-nitraminopyridine (m. 179°) (all with decomposition) heated to 40° in concentrated H2SO4 underwent isomerization to 6,6′-dichloro- (I) (m. 215-17°, yield 10%) and 6,6′-dichloro-2-nitro- (II) (m. 165°, 9%), 2,2′-dichloro- (III) (m. 237-9°, 26%), 5,5′-dichloro- 3, 3′-azopyridine (IV) (m. 183°, 16%) and 5-chloro-3-hydroxypyridine (m. 158°, 32%), and 4,4′-dichloro-3,3′-azopyridine (V) (m. 164°, 40%), resp. I, III, IV, and V with SnCl2, Sn, or NaSH gave the hydrazopyridines, m. 183-5°, 209°, 128-31°, and 172°, resp., yields 70-91%. Reduction of III yielded 6-chloro-2,3-diamino- and -3-aminopyridine. A new method of preparation of 3-amino-5-chloropyridine (VI) was described. Br (32 g.) dissolved in 25 g. NaOH, 50 ml. H2O, and 250 g. ice, 25.5 g. 5-chloronicotinic acid amide added, the mixture heated 0.5 hr. at 75°, the solution saturated with NaCl, extracted with Et2O, dried (K2CO3), and evaporated gave 83% VI, m. 82° (C6H6 + ligroine).

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem