Day: February 10, 2023

Convenient synthesis of tricyclic N(1)-C(2)-fused oxazino-indolones via [Au(I)] catalyzed hydrocarboxylation of allenes was written by Pedrazzani, Riccardo;Pinosa, Emanuele;Bertuzzi, Giulio;Monari, Magda;Lauzon, Samuel;Ollevier, Thierry;Bandini, Marco. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.HPLC of Formula: 167631-84-7 This article mentions the following:

A new [Au(I)] catalyzed intramol. hydrocarboxylation of allenes was presented as a valuable synthetic route to oxazino[4,3-a]indolones I [R = H, Me, c-hexyl; R¹ = H, 8-Me, 8-F, etc.]. The use of 3,5-(CF₃)2-C₆H₃-ImPyAuSbF₆ as the optimal catalyst (5 mol%) was necessary to guarantee (i) wide tolerance of functional groups, (ii) mild reaction conditions (r.t., 16 h), and (iii) high yields (up to 90%). Preliminary attempts toward an enantioselective version (81 : 19 er) were also documented by means of a new family of chiral C₁-sym. ImPyAuCl complexes. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7HPLC of Formula: 167631-84-7).

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.HPLC of Formula: 167631-84-7

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Chemo-selective control of Ritter-type reaction by coordinatively unsaturated inorganic salt hydrates was written by Lai, Huifang;Xu, Jiexin;Lin, Jin;Su, Biling;Zha, Daijun. And the article was included in Organic Chemistry Frontiers in 2022.Application In Synthesis of 2-Phenylisoindolin-1-one This article mentions the following:

The Ritter-type reaction, without relying on a pre-installed functional group, is a highly efficient tool for the construction of amides. However, the intrinsic chemo-selectivity that determines the generation of amides or byproducts limits the efficiency and yield of the reaction. From 68 different types of hydrates studied, a coordinatively unsaturated inorganic salt hydrate, MgSO₄路2H₂O, controlled chemo-selectivity and eliminated the shortcomings of other synthesis approaches. To rationalize the differences in selectivity of inorganic salt hydrates, their corresponding water content, alkalinity, anions and cations were analyzed. MgSO₄路2H₂O was used with diverse scaffolds and C-H oxygenations, which demonstrated its generality in synthetic utility. Because it is readily available and it significantly improves yield, MgSO₄路2H₂O will have broad application for Ritter-type reactions. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application In Synthesis of 2-Phenylisoindolin-1-one).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Application In Synthesis of 2-Phenylisoindolin-1-one

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis and characterization of cytotoxic activity of certain n-(6-benzoyl-1H-benzo [d] imidazol-2-yl)-2-(2-oxoindolin-3-ylidene) hydrazine carboxamides was written by Rani, B. Shoba;Priyanka, K. Blessi;Sammaiah, G.. And the article was included in International Journal of Pharmacy and Biological Sciences in 2014.Formula: C8H4N2O4 This article mentions the following:

A series of N-(6-benzoyl-1H-benzo[d]imidazol-2-yl)-2-(2-oxoindolin-3-ylidene) hydrazine carboxamides I [R = H, 5-CH₃, 5-Cl, 5-Br, 5-NO₂, 7-NO₂, 7-CH₃] were synthesized by treating (5-benzoyl-1H-benzo[d]imidazol-2-yl) carbamates II with different substituted isatins. All the synthesized derivatives I were screened for anticancer activity against Hela using MTT assay and produced a dose dependent inhibition of growth of the cells. The IC₅₀ values of all the synthetic test compounds were found between 16.03 to 41.75. The potency of (IC₅₀ values) of cytotoxicity of compounds was compared with that of known cytotoxic agent, Cisplatin. Among all the synthesized novel compound I (R = 5-Cl) showed the most potent activity against MCF-7 cell lines. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Formula: C8H4N2O4).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C8H4N2O4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Application of the mild-condition phthalimidine synthesis with use of 1,2,3-1H-benzotriazole and 2-mercaptoethanol as dual synthetic auxiliaries. Effective synthesis of phthalimidines possessing a variety of substituents at 2-position was written by Takahashi, Ichiro;Kawakami, Teruki;Hirano, Etsushi;Kimino, Mako;Kamimura, Shigeki;Miwa, Takayuki;Tamura, Takanori;Tazaki, Ryo;Kitajima, Hidehiko;Hatanaka, Minoru;Isa, Kimio;Hosoi, Shinzo. And the article was included in Heterocycles in 2016.Reference of 5388-42-1 This article mentions the following:

Synthesis of 2-substituted phthalimidines (2,3-dihydroisoindol-1-one) I [R = t-Bu, C⁶H⁵, c-C⁶H¹¹, etc.] were described via Mannich type condensation reaction between o-phthalaldehyde with a variety of primary amines in the presence of excess 2-mercaptoethanol and 1,2,3-1H-benzotriazole as dual synthetic auxiliaries. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Reference of 5388-42-1

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis of some symmetric disulfides from thiophthalimides and amines under microwave irradiation was written by Yakan, Hasan;Karakullukcu, Nalan Turkoz;Cakmak, Sukriye;Kutuk, Halil. And the article was included in Research Journal of Chemistry and Environment in 2018.HPLC of Formula: 14204-27-4 This article mentions the following:

Some sym. disulfides were astonishingly prepared from thiophthalimides (sulfenimides) and amines in the presence of 2-ethoxyethanol (尾-ee, neat) at microwave irradiation under free catalyst and ligand. The products were obtained in good to excellent yields ranging from 62% to 92%. When only thiophthalimides were exposed to microwave irradiation, disulfides were not obtained. Also, disulfides were not obtained from thiophthalimides in the presence of 2-ethoxyethanol (neat) under microwave irradiation The microwave-assisted synthesis method was compared with the classical method. The products obtained were purified with chromatog. method and the anal. of them was performed with IR, ¹H NMR, ¹³C NMR spectroscopic and elemental methods. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4HPLC of Formula: 14204-27-4).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.HPLC of Formula: 14204-27-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Antibacterial and cytotoxic activity of 3, 3′-(5,5′-methylene bis(3-mercapto-4H-1,2,4-triazole-5,4-diyl) bis (azan-1-yl-1-ylidene) diindolin-2-ones was written by Rani, S. Shobha;Ajitha, M.;Agaiah, Bairi;Sarangapani, M.. And the article was included in Journal of Chemical and Pharmaceutical Sciences in 2010.Related Products of 112656-95-8 This article mentions the following:

Indolinones I (R¹ = H, R² = 5-F, 5-Me, 6-Br, etc.) were synthesized by the condensation of an appropriate isatin with 5,5¹-methylenediyl-bis(4-amino-4H-1,2,4-triazole-3-thiol). Compounds I were screened for cytotoxic activity using A-549 Lung cancer and HT-29 Colon cancer cell lines by MTT method and antibacterial activity against B. subtilis, S. aureus, E. coli and S. typhi by cup plate method. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Related Products of 112656-95-8).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Related Products of 112656-95-8

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Discovery of a New Class of Anilinoquinazoline Inhibitors with High Affinity and Specificity for the Tyrosine Kinase Domain of c-Src was written by Ple, Patrick A.;Green, Tim P.;Hennequin, Laurent F.;Curwen, Jon;Fennell, Michael;Allen, Jack;Lambert-van der Brempt, Christine;Costello, Gerard. And the article was included in Journal of Medicinal Chemistry in 2004.Quality Control of 1-Methyl-1H-indol-4-amine This article mentions the following:

Deregulated activity of the nonreceptor tyrosine kinase c-Src is believed to result in signal transduction, cytoskeletal and adhesion changes, ultimately promoting a tumor-invasive phenotype. We report here the discovery of a new class of anilinoquinazoline inhibitors with high affinity and specificity for the tyrosine kinase domain of the c-Src enzyme. Special attention was directed toward finding inhibitors selective against KDR tyrosine kinase in order to ensure that the in vivo profile of a specific Src inhibitor could be determined The 4-aminobenzodioxole quinazoline series gave compounds with excellent potency and selectivity. The most interesting compounds were evaluated in vivo and displayed good pharmacokinetics following oral dosing. Compounds such as the aminobenzodioxoles were shown to be potent inhibitors of tumor growth in a c-Src-transformed 3T3 xenograft model in vivo, resulting in more than 90% growth inhibition at doses as low as 6 mg/kg po once daily. Src tyrosine kinase inhibitors such as these may provide a novel therapeutic modality for targeting cancer invasion and metastasis. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indol-4-amine (cas: 85696-95-3Quality Control of 1-Methyl-1H-indol-4-amine).

1-Methyl-1H-indol-4-amine (cas: 85696-95-3) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Quality Control of 1-Methyl-1H-indol-4-amine

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Effect of tetramethylethlylenediamine on the metalation of N-methyl and N-phenylbenzylamine with n-butyllithium. Deuteration and electrophilic condensations of intermediate lithioamines. Cyclodehydrations to give N-substituted isoindolines was written by Ludt, Robert E.;Hauser, Charles R.. And the article was included in Journal of Organic Chemistry in 1971.Application of 5388-42-1 This article mentions the following:

PhCH2NHMe underwent dimetalation with BuLi-Me2NCH2CH2NMe2 (TMEDA) predominantly at the N and the o-benzyl positions as evidenced by deuteration studies. The intermediate o-LiC6H4CH2NMeLi was condensed with BzPh, BzH, cyclohexanone, BzMe, and BzEt. The resulting o-carbinolamines from the BzPh and BzH condensations underwent acid-catalyzed cyclodehydration to form N-methylisoindoline derivatives, while the ortho codensation products from the latter 3 ketones underwent acid-catalyzed linear dehydration reactions, rather than cyclodehydration to form isoindolines. N-Phenylbenzylamine was similarly dimetalated at the N and o-benzyl positions with TMEDA activated BuLi. o-Carbonyl addition reactions of the dilithio amine intermediate with CO2, BzPh, BzH, and 9-fluorenone resulted in an acid and o-carbinolamines, which were readily cyclodehydrated to N-phenylphthalimidine and N-phenylisoindoline derivatives In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application of 5388-42-1).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Application of 5388-42-1

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

C-H Bond Alkylation of Cyclic Amides with Maleimides via a Site-Selective-Determining Six-Membered Ruthenacycle was written by Yuan, Yu-Chao;Goujon, Marion;Bruneau, Christian;Roisnel, Thierry;Gramage-Doria, Rafael. And the article was included in Journal of Organic Chemistry in 2019.Product Details of 5388-42-1 This article mentions the following:

The first example of a ruthenium-catalyzed C-H bond alkylation via six-membered ruthenacycles is presented. This is disclosed for the C-H bond alkylation of biol. relevant cyclic amides with maleimide derivatives The cyclic tertiary amide core acted as a directing group (DG) enabling formation of six-membered cycloruthenated species responsible for the control of the regio- and site selectivity of the reaction as well as the excellent functional group tolerance. Unexpectedly, cyclic amides were found to be better DGs than pyridine-containing ones or cyclic imides for this type of C-H bond functionalization. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Product Details of 5388-42-1).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Product Details of 5388-42-1

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Structural studies on monohalogenated derivatives of the phytohormone indole-3-acetic acid (auxin) was written by Nigovic, Biljana;Kojic-Prodic, Biserka;Antolic, Snjezana;Tomic, Sanja;Puntarec, Vitomir;Cohen, Jerry D.. And the article was included in Acta Crystallographica, Section B: Structural Science in 1996.Synthetic Route of C10H8ClNO2 This article mentions the following:

The physiol. properties of the phytohormone (auxin) indole-3-acetic acid (IAA) and its ring substituted derivatives have so far been rationalized by a number of contradictory hypotheses based on incomplete structural data deduced mainly by inspection of mol. models. To give more evidence for structure-activity relations of monohalogenated IAA’s, the mol. structures of the natural auxin 4-Cl-IAA as well as 5-Cl-IAA, 6-Cl-IAA, 7-Cl-IAA and 5-Br-IAA are compared, as revealed by x-ray anal., and mol. mechanics and dynamics. The influence of the substitution site and the size of the halogen atom and bioactivity is discussed. The typical structural feature of the mols. studied is the slight distortion of part of the indole nucleus around C7: bond length C6-C7 1.368(6) 脜 and C6-C7-C71 117.6(3)掳 (average values of five structures and seven mols.). The conformations of monohalogenated indole-3-acetic acid mols., characteristic for auxins, are defined by rotations about two bonds only: one describes the relative orientation of a side chain towards the indole moiety and the 2nd the orientation of the carboxylic group. The results of x-ray structure anal., and mol. mechanics and dynamics revealed the folded shape of the mols. in all compounds studied. Ab initio calculations showed that the planar conformation can be adopted as well. Crystal data at 297 K for 4-Cl-IAA, 6-Cl-IAA, 7-Cl-IAA and 5-Br-IAA, and at 220 K for 5-Cl-IAA are as follows: 4-Cl-IAA, monoclinic, space group P2₁/c, a 7.313(4), b 17.156(4), c 7.640(4) 脜, 尾 92.71(5)掳, Z = 4, d_c = 1.454, R = 0.037, R_w = 0.039 for 1040 reflections; 5-Cl-IAA, monoclinic, space group P2₁/c, a 19.141(4), b 5.154(2), c 10.323(3) 脜, 尾 116.23(2)掳, Z = 4, d_c = 1.524, R = 0.039, R_w = 0.042 for 1184 reflections; 6-Cl-IAA, orthorhombic, space group Pbca, a 61.08(1), b 12.115(7), c 7.674(5) 脜, Z = 8 (3 mols./Z), d_c = 1.471, R = 0.052, R_w = 0.052 for 3030 reflections; 7-Cl-IAA, monoclinic, space group P2₁/c, a 20.244(5), b 4.829(2), c 10.728(4) 脜, 尾 116.30(1)掳, Z = 4, d_c = 1.481, R = 0.042, R_w = 0.029 for 889 reflections; 5-Br-IAA, triclinic, space group P1虆, a 5.645(3), b 9.713(4), c 10.019(4) 脜, 伪 116.02(3), 尾 92.67(5), 纬 100.12(4)掳, Z = 2, d_c = 1.754, R = 0.029, R_w = 0.020 for 1865 reflections. At. coordinates are given. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Synthetic Route of C10H8ClNO2).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Synthetic Route of C10H8ClNO2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles