06/02/2023 - Page 2 of 2 - Indole Building Blocks

Kim, Moon H. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2012 | CAS: 320734-35-8

7-Bromooxindole (cas: 320734-35-8) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.COA of Formula: C8H6BrNO

The design, synthesis, and biological evaluation of potent receptor tyrosine kinase inhibitors was written by Kim, Moon H.;Tsuhako, Amy Lew;Co, Erick W.;Aftab, Dana T.;Bentzien, Frauke;Chen, Jason;Cheng, Wei;Engst, Stefan;Goon, Levina;Klein, Rhett R.;Le, Donna T.;Mac, Morrison;Parks, Jason J.;Qian, Fawn;Rodriquez, Monica;Stout, Thomas J.;Till, Jeffrey H.;Won, Kwang-Ai;Wu, Xiang;Michael Yakes, F.;Yu, Peiwen;Zhang, Wentao;Zhao, Yeping;Lamb, Peter;Nuss, John M.;Xu, Wei. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.COA of Formula: C8H6BrNO This article mentions the following:

Variously substituted indolin-2-ones were synthesized and evaluated for activity against KDR, Flt-1, FGFR-1 and PDGFR. Extension at the 5-position of the oxindole ring with Et piperidine (I) proved to be the most beneficial for attaining both biochem. and cellular potencies. Further optimization of I to balance biochem. and cellular potencies with favorable ADME/ PK properties led to the identification of II, a compound with a clean CYP profile, acceptable pharmacokinetic and toxicity profiles, and robust efficacy in multiple xenograft tumor models. In the experiment, the researchers used many compounds, for example, 7-Bromooxindole (cas: 320734-35-8COA of Formula: C8H6BrNO).

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

Ha, Jae Du et al. published their research in Journal of the American Chemical Society in 1999 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.COA of Formula: C14H9NO2S

Total Synthesis of Clavepictines A and B. Diastereoselective Cyclization of δ-Aminoallenes was written by Ha, Jae Du;Cha, Jin Kun. And the article was included in Journal of the American Chemical Society in 1999.COA of Formula: C14H9NO2S This article mentions the following:

The stereocontrolled total synthesis of (-)-clavepictine A (I) and (+)-clavepictine B (II) has been accomplished in an enantioselective fashion, which has unequivocally established the absolute configuration of I and II. The pivotal step in the synthesis is diastereoselective silver(I)-promoted cyclization of δ-amino allenes. Another key method includes cross-coupling of enol triflates of N-acyl lactams, which allows stereocontrolled functionalization of otherwise unreactive lactams under mild conditions. The utility of Beak’s α-lithiation-substitution chem. of N-BOC piperidines involving a functionalized aldehyde as the electrophile is demonstrated in the preparation of highly substituted nitrogen heterocycles. These new synthetic strategies should be of general synthetic utility in the stereoselective syntheses of quinolizidines, indolizidines, and related aza-heterocycles. Also included is the unique conformational preference of the highly substituted cis-quinolizidine core of clavepictines; the (superfluous) m-(trifluoromethyl)benzoate substituent has a surprisingly significant influence on the relative energies of the two possible chair-chair conformations. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4COA of Formula: C14H9NO2S).

Nametkin, N. S. et al. published their research in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya in 1982 | CAS: 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.Name: 2-Phenylisoindolin-1-one

Action of sulfur on μ-[(o-phenylenemethylene)(phenylamino)]diiron hexacarbonyl was written by Nametkin, N. S.;Tyurin, V. D.;Nekhaev, A. I.;Kondrat’eva, M. G.;Sobolev, Yu. P.. And the article was included in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya in 1982.Name: 2-Phenylisoindolin-1-one This article mentions the following:

The title reaction in C₆H₆ at 80° gave S₂Fe₂(CO)₆ 12, S₂Fe₃(CO)₉ 3, I 6, II 33, PhCH(NHPh)₂ 11, Ph₃N 2, III 11, and PhNH₂ 22%. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Name: 2-Phenylisoindolin-1-one).

Ghorab, M. M. et al. published their research in Phosphorus, Sulfur and Silicon and the Related Elements in 1998 | CAS: 24407-32-7

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Category: indole-building-block

Synthesis of some sulfur containing tetrahydrobenzo[b]thieno(pyridines, quinolines, oxazines and pyrimidines) as possible radioprotective and antineoplastic agents was written by Ghorab, M. M.;Nassar, O. M.;Hassan, A. Y.. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 1998.Category: indole-building-block This article mentions the following:

Synthesis of novel benzothienopyridines, benzothienoquinoline, benzothienoxazines and benzothienopyrimidines utilizing 2-methyl-5,6,7,8-tetrahydro-4H-3,1-benzothienoxazine-4-one are reported. Preliminary biol. studies of some compounds showed a promising radioprotection and antineoplastic activities. In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Category: indole-building-block).

Meyer, Kerstin U. et al. published their research in Journal of the Chemical Society, Perkin Transactions 1 in 2001 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 4583-55-5

Novel bis(tetrahydropyrrolo[3,4-b]carbazoles) linked with aliphatic chains: synthesis and structural aspects was written by Meyer, Kerstin U.;Pindur, Ulf. And the article was included in Journal of the Chemical Society, Perkin Transactions 1 in 2001.Recommanded Product: 4583-55-5 This article mentions the following:

Dehydrohalogenation of 2,3-bis(bromomethyl)-1H-indole-1-carboxylic acid Me ester gave 2,3-dihydro-2,3-bis(methylene)-1H-indole-1-carboxylic acid Me ester derivatives Diels-Alder reaction of these 2,3-dihydro-2,3-bis(methylene)-1H-indole-1-carboxylic acid Me ester derivatives with N,N‘-trimethylenedimaleimide, N,N‘-tetramethylenedimaleimide, or N,N‘-dodecamethylenedimaleimide gave 2,2’-(alkanediyl)bis[dioxopyrrolo[3,4-b]carbazolecarboxylate] derivatives (i.e., the title compounds containing aliphatic chain linkages). These conformationally highly flexible mols. represent an interesting class of compounds, believed to have an affinity towards DNA, as potential DNA ligands. Pharmacol. test data were not reported. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Recommanded Product: 4583-55-5).

Porter, William L. et al. published their research in Phytochemistry (Elsevier) in 1965 | CAS: 1912-45-4

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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Related Products of 1912-45-4

Molecular requirements for auxin activity. I. Halogenated indoles and indoleacetic acid was written by Porter, William L.;Thimann, Kenneth V.. And the article was included in Phytochemistry (Elsevier) in 1965.Related Products of 1912-45-4 This article mentions the following:

2-Chloroindoleacetic acid had 350% of the activity of indoleacetic acid (IAA) in the pea curvature test; the 2-bromo analog had 160% activity and the corresponding Me and Et esters were even more active. In a series of these and other IAA derivatives, the log of the growth activity is a linear function of the NH stretching frequency in the ir spectra and of the Hammett sigma value for the substituent. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Related Products of 1912-45-4).

Ma, Dengke et al. published their research in Angewandte Chemie, International Edition in 2019 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C10H10BrN

Organocatalytic Enantioselective Functionalization of Unactivated Indole C(sp³)-H Bonds was written by Ma, Dengke;Zhang, Zhihan;Chen, Min;Lin, Zhenyang;Sun, Jianwei. And the article was included in Angewandte Chemie, International Edition in 2019.Computed Properties of C10H10BrN This article mentions the following:

Described here is a direct catalytic asym. functionalization of unactivated alkyl indoles using organocatalysis. In the presence of an effective chiral urea catalyst and a phosphoric acid additive, the intermol. C-C bond formation between alkyl indoles and trifluoropyruvates proceeded with high efficiency and enantiocontrol. Unlike previous asym. C(sp³-H) functionalizations of α-azaarenes, this process does not require the use of either a strong base or an electron-deficient substrate. The excellent enantiocontrol is particularly noteworthy in view of the severe background reaction as well as the complete inability of other types of catalysts evaluated. Control experiments, kinetic studies, and DFT calculations provided important insights into the mechanism. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Computed Properties of C10H10BrN).

Coyle, Robert et al. published their research in Journal of Organic Chemistry in 2014 | CAS: 6639-06-1

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Category: indole-building-block

Tandem Reactions via Barton Esters with Intermolecular Addition and Vinyl Radical Substitution onto Indole was written by Coyle, Robert;McArdle, Patrick;Aldabbagh, Fawaz. And the article was included in Journal of Organic Chemistry in 2014.Category: indole-building-block This article mentions the following:

A one-pot initiator-free Barton ester decomposition with tandem radical addition onto alkyl propiolates or phenylacetylene with aromatic substitution of the resultant vinyl radical allows convenient access to new 9-substituted 6,7-dihydropyrido[1,2-a]indoles, e.g., I (X = Me, CHO, CN; R = Me, Et, t-Bu). Pr radical cyclizations compete when forming the expanded 7,8-dihydro-6H-azepino[1,2-a]indole system. 2-Thiopyridinyl S-radical is incorporated into aromatic adducts when using unsubstituted indole-1-alkanoic acid precursors. X-ray crystallog. on substitution products allows selectivity of the radical addition onto less reactive internal alkynes to be determined In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Category: indole-building-block).

Oseka, Maksim et al. published their research in Organic Letters in 2016 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Synthetic Route of C8H4N2O4

Asymmetric Organocatalytic Wittig [2,3]-Rearrangement of Oxindoles was written by Oseka, Maksim;Kimm, Mariliis;Kaabel, Sandra;Jarving, Ivar;Rissanen, Kari;Kanger, Tonis. And the article was included in Organic Letters in 2016.Synthetic Route of C8H4N2O4 This article mentions the following:

A highly enantioselective organocatalytic [2,3]-rearrangement of oxindole derivatives is presented. The reaction was catalyzed by squaramide, and this provides access to 3-hydroxy 3-substituted oxindoles I and II (Ar = Ph, 4-ClC₆H₄, 3-ClC₆H₄, 2-ClC₆H₄, 4-MeOC₆H₄, 4-NO₂C₆H₄, 2-thienyl, 2-naphthyl, etc.; R¹ = H, 5-F, 7-F, 5-MeO, 5-Br, 7-NO₂, etc.; R² = H, Bn, Me, i-Pr, 4-MeC₆H₄CH₂) in high enantiomeric purities. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Synthetic Route of C8H4N2O4).

Foa, M. et al. published their research in Journal of Organometallic Chemistry in 1985 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Quality Control of 2-Phenylisoindolin-1-one

Cobalt-catalyzed carbonylation of aryl halides was written by Foa, M.;Francalanci, F.;Bencini, E.;Gardano, A.. And the article was included in Journal of Organometallic Chemistry in 1985.Quality Control of 2-Phenylisoindolin-1-one This article mentions the following:

Carbonylation of aromatic and heteroaromatic halides with a catalytic system of alkylcobalt carbonyl complexes, either preformed or made in situ, and bases such as alkoxides, NaOH, and K₂CO₃ in aliphatic alcs produced aromatic esters, acids, lactones, and lactams in high yield and under mild conditions. New anionic cobalt complexes were formed which were characterized by high reactivity toward aromatic halides. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Quality Control of 2-Phenylisoindolin-1-one).