Month: April 2022

Computed Properties of C10H11NO2. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid, is researched, Molecular C10H11NO2, CAS is 114527-53-6, about Structure-based design of 3-carboxy-substituted 1,2,3,4-tetrahydroquinolines as inhibitors of myeloid cell leukemia-1 (Mcl-1).

Mcl-1 has recently emerged as an attractive target to expand the armamentarium in the war on cancer. Using structure-based design, 3-carboxy-substituted 1,2,3,4-tetrahydroquinolines were developed as a new chemotype to inhibit the Mcl-1 oncoprotein. The most potent compound inhibited Mcl-1 with a Ki of 120 nM, as determined by a fluorescence polarization competition assay. Direct binding was confirmed by 2D 1H-15N HSQC NMR spectroscopy with 15N-Mcl-1, which indicated that interactions with R263 and T266, and occupation of the p2 pocket are likely responsible for the potent binding affinity. The short and facile synthetic chem. to access target mols. is expected to mediate lead optimization.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthetic sympatholytic substances in the ergotamine series. V. Some derivatives of 1,2,3,4-tetrahydroquinoline》. Authors are Chiavarelli, Stefano; Marini-Bettol, G. B..The article about the compound:1,2,3,4-Tetrahydroquinoline-3-carboxylic acidcas:114527-53-6,SMILESS:OC(=O)C1CNC2=CC=CC=C2C1).Related Products of 114527-53-6. Through the article, more information about this compound (cas:114527-53-6) is conveyed.

cf. C.A. 46, 5602g. In connection with investigations aimed at establishing the relations between the chem. structure and biol. activity of compounds of the type of the alkaloids of Segale cornuta, it seemed of interest to study some 3-substituted derivatives of 1,2,3,4-tetrahydroquinoline (I), particularly since the structure of I is found in the lysergic acid mol. By a modification of the method of Gilman and Spatz (C.A. 35, 5495.2), 83 g. 3-quinolinecarboxylic acid (II), m. 275-6°, was obtained by refluxing 108 g. 3-cyanoquinoline (III) and 20% aqueous NaOH 2 hrs. The Na salt of II (25 g.) in 200 cc. water and 5 g. Raney Ni, hydrogenated 2 hrs. at 150° and 120 atm., filtered, the filtrate concentrated, acidified with HCl (d. 1.17) (to Congo red), and the precipitate purified by dilute EtOH yield 14 g. 1,2,3,4-tetrahydro-3-quinolinecarboxylic acid-HCl (IV), m. 236°, which with NH4OH yields the free acid, m. 145-6° (from EtOH). IV (0.2 g.) in 3 cc. anhydrous C5H5N and 1.6 g. Ac2O, refluxed 10 min., poured when cool into 10 cc. water + 6 cc. HCl, allowed to stand, and the precipitate purified by EtOH, yield the 1-Ac derivative, C12H14O2N, straw-colored, m. 152°. A suspension of 100 g. III in 1400 cc. MeOH refluxed 10 hrs. in a current of HCl gas (III.HCl forms first), most of the MeOH distilled, the residue poured into 3 l. ice-water, made alk. with K2CO3, kept ice-cold several hrs., and the precipitate purified by MeOH, yields 82 g. of Me 3-quinolinecarboxylate (V), m. 73-4°. V (36 g.) in 300 cc. MeOH with 5 g. Pd-C, hydrogenated at 60-65° under 90 atm., filtered, concentrated in vacuo, and allowed to stand, yields Me dihydro-3-quinolinecarboxylate (VI), m. 134-5°, is strongly fluorescent in Wood light (both solid and in solution), reduces neutral AgNO3 solution, is oxidized by dilute KMnO4; picrate, m. 187-9°. V (2 g.) in 50 cc. MeOH with 2 g. Raney Ni, hydrogenated 3 hrs. at 110° under 100 atm., filtered, and distilled at 115° (0.1 mm.); or 5 g. VI in 100 cc. MeOH with 4 g. Raney Ni and 1 g. 10% Pd-C, hydrogenated at 100° under 100 atm., and the product filtered, concentrated, and distilled in vacuo, yields the 1,2,3,4-tetrahydro derivative (VII), of VI, viscous oil, b0.3 124°. With HCl, it forms an HCl salt, m. 181-4°, and with picric acid a picrate, m. 151-3°. VII (1 g.) and 5-8 cc. concentrated HCl, heated in a sealed tube 3 hrs. at 100°, and the product purified by dilute EtOH, yield 1,2,3,4-tetrahydro-3-quinolinecarboxylic acid-HCl (VIII), m. 234°. N,N-Diethyl-3-quinolinecarboxamide (IX) (10 g.) in 100 cc. MeOH with 3 g. 10% Pd-C, hydrogenated 3 hrs. at 60° under 90 atm., filtered, concentrated, and the precipitate purified by EtOH, yields 1,2,3,4-tetrahydro derivative (X), m. 132-3°, forming with HCl a HCl salt, m. 160-1°. Hydrolyzed like VII, X yields VIII, m. 235-6°. 3-Aminoquinoline (XI) (144 g.) in 400 cc. tetrahydronaphthalene with 15 g. Raney Ni, hydrogenated at 55° under 90 atm., filtered, distilled in vacuo, and the residue rectified in vacuo, yields 127 g. crude product, b8 160-6°, which, fractionated and the fractions b. above 164° distilled in vacuo (0.8 mm.) at 250°, yields the 1,2,3,4-tetrahydro derivative (XII), m. 57°; picrate (from anhydrous EtOH), m. 205-6°; HCl salt (from EtOH by addition of Et2O), sinters 240°, m. 250°, turns violet by oxidation in air. XII oxidizes easily on exposure to air and light, and shows triboluminescence when rubbed with a wooden spatula. Benzoylated by the Schotten-Bauman method, XII gives a di-Bz derivative, C23H20O2N2, m. 201° (from EtOH). The distillation residue of XII (a fraction, b0.8 250°), fractionated further, gives a fraction, b0.4 234°, 3,3′-iminobis(1,2,3,4-tetrahydroquinoline) (XIII), very viscous resinous oil. With HCl, it forms a HCl salt (XIV), m. 254°, and with picric acid a picrate, m. 190-2°. In aqueous HCl solution, XIV gives with aqueous NaNO2 a yellow precipitate, which, purified by EtOH, yields the nitroso derivative, C18H18O3N6, m. 156°. Et2SO4 (9 cc.), added during 1 hr. to 15 g. XII in 200 cc. anhydrous Me2CO and 16 g. K2CO3, the mixture refluxed 6 hrs., filtered, evaporated, excess 20% aqueous NaOH added, the solution extracted with Et2O, the extract dried by K2CO3, evaporated, and the residue distilled in vacuo, yields 3-ethylamino-1,2,3,4-tetrahydroquinoline, b0.1 110-13°; picrate (from anhydrous EtOH), m. 198°. Et2SO4 (28 cc.), added during 1 hr. to 15 g. XII in 300 cc. anhydrous Me2CO and 48 g. K2CO3, the mixture refluxed 8 hrs., and the foregoing procedure followed, yields 3-diethylamino-1-ethyl-1,2,3,4-tetrahydroquinoline, b0.4 116°; picrate, m. 103-4°; HCl salt, very hygroscopic. The ultraviolet absorption spectra of II, IV, V, VI, VII, IX, X, XI, and XII are reproduced.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Category: thiazolidine. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Some mercuration reactions of substituted pyrroles.

Mercuration of N-unsubstituted pyrroles with mercury(II) acetate results in immediate precipitation of the N-mercurated derivative, which is insoluble in virtually all organic solvents. If the pyrrole N atom is protected (e.g. with Me, CH2OCH2Ph, or CO2CMe3) then mercuration takes place efficiently at unsubstituted pyrrole carbons. Subsequent palladium/olefin (Heck-type) reactions afford the corresponding pyrrole acrylate when, for example, the olefin is Me acrylate; deprotection (when the N-substituent is CH2OCH2Ph or CO2CMe3) then affords the required carbon-substituted pyrrole. Attempts to deprotect the N-methylpyrroles were unsuccessful.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of pyrrolecarboxaldehydes》. Authors are Ghigi, Elisa; Drusiani, Annamaria.The article about the compound:Ethyl 3,5-Dimethyl-2-pyrrolecarboxylatecas:2199-44-2,SMILESS:O=C(C1=C(C)C=C(C)N1)OCC).Computed Properties of C9H13NO2. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

HCO-NMe2 (I) (23.89 g.) and 58.25 g. POCl3 warmed after 10 min. to 60°, treated dropwise in 1.5 hrs. with 18 g. 2,4-dimethylpyrrole in an equal volume of I, the mixture stirred 1 hr. at 60°, poured into 333 g. ice and 245 g. fused NaOAc, the mixture boiled, cooled, extracted with Et2O, the extract evaporated free from Et2O and made alk. with powd. Na2CO3, filtered, and the residual product (II) dried. Further extraction of the filtrate with Et2O gave another 0.69 g. II. II boiled in petr. ether, the solution purified with C, filtered and cooled gave 0.6 g. (crude) 2,4-dimethyl-3,5-pyrroledicarboxaldehyde, m. 165-6° (from H2O), and 9.6 g. (crude) 2,4-dimethyl-5-pyrrolecarboxaldehyde, m. 89-90° (from H2O). Similarly, I and POCl3 at 60°, treated dropwise with stirring with 2,4-dimethyl-8-ethylpyrrole gave 2,4-dimethyl-3-ethyl-5-pyrrolecarboxaldehyde, m. 105-6°. In the same way, 1.79 g. I and 4.37 g. POCl3 treated with 1.35 g. 2,3,4-trimethylpyrrole gave 0.3 g. 2,3,4-trimethyl-5-pyrrolecarboxaldehyde, m. 147°; 2.6 g. I and 6.32 g. POCl3 with 3 g. Et 2,4-dimethyl-3-pyrrolecarboxylate in I yielded Et 2,4-dimethyl-5-formyl-3-pyrrolecarboxylate, m. 165°; 8.6 g. I and 21 g. POCl3 with 10 g. Et 2,4-dimethyl-5-pyrrolecarboxylate and 10 g. I produced 11.2 g. Et 2,4-dimethyl-3-formyl-5-pyrrolecarboxylate, m. 145°. Heating 20 g. 2,4-dimethyl-5-carbethoxy-3-pyrrolecarboxylate at 200° with 200 g. quinoline and 2 g. finely divided pure Cu to cessation of CO2 evolution, cooling, filtering, acidifying the filtrate with 50% HCl, filtering, washing the precipitate with H2O, and drying gave 11.2 g. Et 2,4-dimethyl-5-pyrrolecarboxylic acid, m. 122°.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Comparative Study, Article, Hoppe-Seyler’s Zeitschrift fuer Physiologische Chemie called The metabolism of tryptophan and 7-chlorotryptophan in Pseudomonas pyrrocinia and Pseudomonas aureofaciens, Author is Luebbe, Claus; Van Pee, Karl Heinz; Salcher, Olga; Lingens, Franz, which mentions a compound: 63352-97-6, SMILESS is O=C(O)CC1=CNC2=C1C=CC=C2Br, Molecular C10H8BrNO2, HPLC of Formula: 63352-97-6.

P. pyrrocinia ATCC 15958 and a mutant strain (ACN) of P. aureofaciens ATCC 15926 possess a mechanism for the degradation of the tryptophan side chain. Indole, indole-3-carboxylic acid, indole-3-acetic acid, the corresponding compounds chlorinated or brominated at position 7, indole-3-pyruvate, and 7-chloroindole-3-pyruvate were isolated from bacterial cultures. The chlorinated indole derivatives were isolated after the addition of 7-chloro-DL-tryptophan to cultures of P. pyrrocinia whereas their bromo analogs were found in the culture medium of the mutant strain ACN of P. aureofaciens, grown in the presence of NaBr. Enzymic studies show that tryptophan is transaminated to indole-3-pyruvate, which is transformed to indole-3-acetaldehyde. Dehydrogenation of indole-3-acetaldehyde leads to indole-3-acetic acid, which is further metabolized to indole-3-carboxaldehyde and converted by dehydrogenation to indole-3-carboxylic acid. Indole is formed by the spontaneous decarboxylation of indole-3-carboxylic acid.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Recommanded Product: 2199-44-2. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Synthesis of cyanopyrroles. Author is Cheng, Ling Jiang; Lightner, David A..

Regioselective synthesis of α-cyanopyrroles (vs. α-alkoxycarbonylpyrroles) using oximinocyanoacetate esters in a Knorr-type reductive condensation with β-diketones can be directed by the presence of water. Thus, HON:C(CN)CO2Me was reacted with CH2Ac2 in hot AcOH in the presence of Zn dust to give exclusively 3,5-dimethylpyrrole-2-carbonitrile when the AcOH was wet. Whereas, in glacial AcOH, only Me 3,5-dimethylpyrrole-2-carboxylate was isolated in ∼40% yield.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Application In Synthesis of Bromoferrocene. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Electrochemical Parameterization in Sandwich Complexes of the First Row Transition Metals. Author is Lu, Shuangxing; Strelets, Vladimir V.; Ryan, Matthew F.; Pietro, William J.; Lever, A. B. P..

Applying the ligand electrochem. parameter approach to sandwich complexes and standardizing to the FeIII/FeII couple, the authors obtained EL(L) values for over 200 π-ligands. Linear correlations exist between formal potential (E°) and the ∑EL(L) for each metal couple. In this fashion, the authors report correlation data for many first row transition metal couples. The correlations between the EL(L) of the substituted π-ligand and the Hammett substituent constants (σp) are also explored.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Application In Synthesis of Bromoferrocene. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Efficient Two-Electron Reduction of Dioxygen to Hydrogen Peroxide with One-Electron Reductants with a Small Overpotential Catalyzed by a Cobalt Chlorin Complex. Author is Mase, Kentaro; Ohkubo, Kei; Fukuzumi, Shunichi.

A Co chlorin complex (CoII(Ch)) efficiently and selectively catalyzed two-electron reduction of dioxygen (O2) by 1-electron reductants (ferrocene derivatives) to produce H2O2 (H2O2) in the presence of HClO4 (HClO4) in benzonitrile (PhCN) at 298 K. The catalytic reactivity of CoII(Ch) was much higher than that of a Co porphyrin complex (CoII(OEP), OEP2- = octaethylporphyrin dianion), which is a typical porphyrinoid complex. The two-electron reduction of O2 by 1,1′-dibromoferrocene (Br2Fc) was catalyzed by CoII(Ch), whereas virtually no reduction of O2 occurred with CoII(OEP). CoII(Ch) is more stable than CoII(OEP), where the catalytic turnover number (TON) of the two-electron reduction of O2 catalyzed by CoII(Ch) exceeded 30000. The detailed kinetic studies revealed that the rate-determining step in the catalytic cycle is the proton-coupled electron transfer reduction of O2 with the protonated CoII(Ch) ([CoII(ChH)]+) that is produced by facile electron-transfer reduction of [CoIII(ChH)]2+ by ferrocene derivative in the presence of HClO4. The 1-electron-reduction potential of [CoIII(Ch)]+ was pos. shifted from 0.37 V (vs. SCE) to 0.48 V by the addition of HClO4 due to the protonation of [CoIII(Ch)]+. Such a pos. shift of [CoIII(Ch)]+ by protonation resulted in enhancement of the catalytic reactivity of [CoIII(ChH)]2+ for the two-electron reduction of O2 with a lower overpotential as compared with that of [CoIII(OEP)]+.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Related Products of 1273-73-0. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Electron-transfer properties of a nonheme manganese(IV)-oxo complex acting as a stronger one-electron oxidant than the iron(IV)-oxo analogue. Author is Yoon, Heejung; Morimoto, Yuma; Lee, Yong-Min; Nam, Wonwoo; Fukuzumi, Shunichi.

Electron-transfer properties of a nonheme Mn(iv)-oxo complex, [(Bn-TPEN)MnIV(O)]2+, reveals that Mn(iv)-oxo complex acts as a stronger 1-electron oxidant than the Fe(iv)-oxo analog. As a result, an electron transfer process in N-dealkylation was detected by a transient radical cation intermediate, para-Me-DMA√+, in the oxidation of para-Me-DMA by [(Bn-TPEN)MnIV(O)]2+.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Safety of Bromoferrocene. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Action of halogens on ferrocenylgold-triphenylphosphine.

Ph3P.AuC5H4FeC5H5 (I) brominated in CCl4 at -20° to a blue, then yellow material and after evaporation gave 55% bromoferrocene and 18% biferrocenyl along with 70% Ph3P.AuBr. Similar results were obtained at -50° in CH2Cl2. I chlorinated as above to 26% chloroferrocene, 70% biferrocenyl, and 98% Ph3P.AuCl. Iodination gave 82% iodoferrocene and 89% Ph3P.AuI.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com