10/02/2023 - Page 3 of 13 - Indole Building Blocks

Kumar, Dalip et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2011 | CAS: 90271-86-6

5-Bromo-3-cyanoindole (cas: 90271-86-6) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Computed Properties of C9H5BrN2

Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles was written by Kumar, Dalip;Kumar, N. Maruthi;Chang, Kuei-Hua;Gupta, Ritika;Shah, Kavita. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Computed Properties of C9H5BrN2 This article mentions the following:

A series of 3,5-bis(indolyl)-1,2,4-thiadiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. Indole-3-thiocarboxamides, e.g., I, reacted with iodobenzene diacetate via oxidative dimerization to give 3,5-bis(indolyl)-1,2,4-thiadiazoles, e.g., II. Among the synthesized bis(indolyl)-1,2,4-thiadiazoles, the compound II with 4-chlorobenzyl and methoxy substituents showed the most potent activity. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Computed Properties of C9H5BrN2).

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

Zhang, Guangji et al. published their research in ACS Sustainable Chemistry & Engineering in 2020 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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. 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). Synthetic Route of C8H6N2O2

Co,N-Codoped Porous Carbon-Supported Co_yZnS with Superior Activity for Nitroarene Hydrogenation was written by Zhang, Guangji;Tang, Feiying;Wang, Xiaoying;An, Ping;Wang, Liqiang;Liu, You-Nian. And the article was included in ACS Sustainable Chemistry & Engineering in 2020.Synthetic Route of C8H6N2O2 This article mentions the following:

Preparation of chemoselective hydrogenation catalyst containing both CoNx and CoyZnS supported on N-doped porous carbon (CoN_x-Co_yZnS@NPC-Z) was reported. The CoN_x-Co_yZnS@NPC-Z catalyst were prepared by pyrolyzing the protein-metal-ion networks, followed by treatment with acid. The CoN_x-Co_yZnS@NPC-Z-3 catalyst delivered high catalytic activity and selectivity in chemoselective hydrogenation of nitroarenes afforded aryl amines R-NH₂ [R = Ph, 4-ClC₆H₄, 2-naphthyl, etc.] with almost full conversion and >98% selectivity in water/methanol mixture solvents at 90掳C under 5 bar of H₂ pressure for 3h of reaction. Also Schiff-base derivatives R¹CH=NR² [R¹ = Ph, 4-ClC₆H₄, 4-MeOC₆H₄, etc.; R² = Ph, 2-MeC₆H₄, 4-ClC₆H₄, etc.] were prepared via one-pot reductive amination of aryl aldehydes with aromatic nitro compounds using CoN_x-Co_yZnS@NPC-3 catalyst. Notably, the catalytic hydrogenation could work even under 1 bar of H₂ pressure and at room temperature with high conversion and selectivity. Besides, CoN_x-Co_yZnS@NPC-Z-3 exhibited remarkable tolerance to CO or H₂S poisoning and acid erosion. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Synthetic Route of C8H6N2O2).

Ielo, Laura et al. published their research in Advanced Synthesis & Catalysis in 2020 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. 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

Consecutive C1-Homologation / Displacement Strategy for Converting Thiosulfonates into O,S-Oxothioacetals was written by Ielo, Laura;Pillari, Veronica;Miele, Margherita;Holzer, Wolfgang;Pace, Vittorio. And the article was included in Advanced Synthesis & Catalysis in 2020.HPLC of Formula: 14204-27-4 This article mentions the following:

A conceptually intuitive synthesis of oxothioacetals RSCH₂OR¹ [R = Me, Ph, 4-FC₆H₄, 2-F₃CC₆H₄, (4,6-dimethylpyrimidin-2-yl); R¹ = Me, 2-BrC₆H₄, 1-naphthyl, etc.] was reported starting from thiosulfonates as electrophilic sulfur donors. The installation of a reactive CH₂Cl motif with a homologating carbenoid reagent, followed by the immediate nucleophilic displacement with alc. groups [(hetero)-aromatic, aliphatic] offered a convenient access to the title compounds RSCH₂OR¹. Genuine chemoselectivity was uniformly observed in the case of multi-functionalized systems. 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).

Hikawa, Hidemasa et al. published their research in Organic Chemistry Frontiers in 2019 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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. 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.Related Products of 4769-96-4

Platinum(II)-catalyzed dehydrative C3-benzylation of electron-deficient indoles with benzyl alcohols was written by Hikawa, Hidemasa;Matsuura, Yuuki;Kikkawa, Shoko;Azumaya, Isao. And the article was included in Organic Chemistry Frontiers in 2019.Related Products of 4769-96-4 This article mentions the following:

A synthetic strategy for the water-promoted direct dehydrative coupling of indoles I (R = H, Me; R¹ = 6-NO₂, 7-COOH, 5-CN, etc.; R² = H, COOH, phenyl) with benzyl alcs. ArC(OH)(R³)(R⁴) (Ar = C₆H₅, 4-MeOC₆H₄, 3-F₃CC₆H₄, CH=CHC₆H₅, etc.; R³ = Ph, 4-chlorophenyl, Me, etc.; R⁴ = H, Ph) catalyzed by PtCl₂(PhCN)₂ in 1,2-dichloroethane has been developed. Water mols. significantly accelerate C-C bond formation to construct 3-benzylindoles II, whereas the reaction proceeds slowly under anhydrous conditions. Comparative rate plots for reactions in the presence of H₂O and D₂O show a kinetic solvent isotope effect (KSIE) of 1.5. A Hammett study of the dehydrative reaction of para-substituted benzhydrols shows neg. 蟻 values, indicating a build-up of cationic charge during the rate-determining sp³ C-O bond cleavage step. This catalytic system can be used on the gram scale with simplified product isolation and catalysis is performed using 1 mol% of a Pt(II) catalyst with an addnl. mol. of water. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Related Products of 4769-96-4).

6-Nitro-1H-indole (cas: 4769-96-4) 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. 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.Related Products of 4769-96-4

Basarab, Gregory S. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2008 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Quality Control of 5-Chloroindole-3-carboxaldehyde

Design of Helicobacter pylori glutamate racemase inhibitors as selective antibacterial agents: A novel pro-drug approach to increase exposure was written by Basarab, Gregory S.;Hill, Pamela J.;Rastagar, Abdullah;Webborn, Peter J. H.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

High-throughput screening uncovered a pyrazolopyrimidinedione hit as a selective, low micromolar inhibitor of Helicobacter pylori glutamate racemase (MurI). Variation of the substituents around the scaffold led to low nanomolar inhibitors and improved antibacterial activity. The challenge in this program was to translate excellent enzyme inhibition into potent antibacterial activity and pharmacokinetics suitable for oral therapy. Compounds were profiled for MurI inhibition, activity against H. pylori, microsomal stability, and pharmacokinetics in mice. Iterative cycles of analog synthesis and biol. testing led to compounds with substituents optimized for both low MICs (鈮? 渭g/mL) and good microsomal stability. In order to achieve high bioavailability, a novel pro-drug approach was implemented wherein a solubilizing sulfoxide moiety is oxidized in vivo to a sulfone. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

Park, Jin Woo et al. published their research in Bioconjugate Chemistry in 2012 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Formula: C13H17NO3S

Novel Cyanine Dyes with Vinylsulfone Group for Labeling Biomolecules was written by Park, Jin Woo;Kim, YoungSoo;Lee, Kee-Jung;Kim, Dong Jin. And the article was included in Bioconjugate Chemistry in 2012.Formula: C13H17NO3S This article mentions the following:

Novel vinylsulfone cyanine dyes (em. 550-850 nm) were designed and synthesized for fluorescent labeling of biomols. via 1,2-addition reaction in aqueous conditions. Due to the virtue of chem. structures of both fluorophore and reactive group, these dyes could be significantly stable and reactive in various aqueous/organic conditions. A wide variety of pH, temperature, buffer concentration, and protein were tested for the optimal labeling condition. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Formula: C13H17NO3S).

Ravi, Ch. et al. published their research in Russian Journal of Bioorganic Chemistry in 2019 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.Product Details of 827-01-0

Induction of Apoptosis in SKOV3 and DNA Binding by Cobalt(III) Polypyridyl Complexes was written by Ravi, Ch.;Vuradi, Ravi Kumar;Avudoddi, Srishailam;Ramchander, M.;Satyanarayana, S.. And the article was included in Russian Journal of Bioorganic Chemistry in 2019.Product Details of 827-01-0 This article mentions the following:

Abstract: Three new Co(III) polypyridyl complexes [Co(phen)₂CIIP]³⁺ {CIIP = 2-(5-chloro-3a,H-isoindol-3-yl)-1H-imidazo[4,5-f][1,10]phenantholine} (phen = 1,10 phenanthroline), [Co(bpy)₂CIIP]³⁺ (bpy = 2,2′-bipyridine), and [Co(dmb)₂CIIP]³⁺ (dmb = 4,4′-dimethyl-2,2′-bipyridine) were synthesized and characterized by different spectral methods. The complexes interact with DNA in an intercalation mode as confirmed by spectroscopic titration and viscosity measurements. All three complexes cleaved the pBR322 DNA in photoactivated cleavage studies and exhibited good antimicrobial activity. Anticancer activity of these Co(III) complexes was evaluated on the SKOV3 cell line. Cytotoxicity by MTT assay showed growth inhibition in dose dependent manner. Cell cycle anal. by flow cytometry data showed increase in Sub G1 population. Annexin V FITC/PI staining confirmed that these complexes caused cell death by the induction of apoptosis. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Product Details of 827-01-0).

Mino, Takashi et al. published their research in Organic & Biomolecular Chemistry in 2021 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Electric Literature of C8H6N2O2

Cinnamoyl amide type chiral P,olefin ligands for Pd-catalyzed reactions was written by Mino, Takashi;Fujisawa, Yohei;Yoshida, Shizuki;Hirama, Mitsuru;Akiyama, Takumu;Saito, Ryo;Yoshida, Yasushi;Kasashima, Yoshio;Sakamoto, Masami. And the article was included in Organic & Biomolecular Chemistry in 2021.Electric Literature of C8H6N2O2 This article mentions the following:

Cinnamoyl amide type chiral P,olefin ligands are synthesized. Authors successfully obtained separable diastereomers of I with axial chirality and demonstrated Pd-catalyzed asym. allylic substitution reactions of indoles using compound I as a chiral ligand with high enantioselectivities (up to 98% ee). In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Electric Literature of C8H6N2O2).

Wang, Qinghui et al. published their research in European Journal of Medicinal Chemistry in 2018 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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. 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.Safety of 6-Nitro-1H-indole

Synthesis and biological evaluation of indole-based UC-112 analogs as potent and selective survivin inhibitors was written by Wang, Qinghui;Arnst, Kinsie E.;Xue, Yi;Lei, Zi-Ning;Ma, Dejian;Chen, Zhe-Sheng;Miller, Duane D.;Li, Wei. And the article was included in European Journal of Medicinal Chemistry in 2018.Safety of 6-Nitro-1H-indole This article mentions the following:

The extensive structural modification of the recently discovered selective survivin inhibitor UC-112 and the synthesis of thirty-three new analogs I [R = (5-fluoro-1H-indazol-1-yl)methyl, 7-fluoro-indol-1-ylmethyl, 2-methyl-5-methoxy-indol-1-ylmethyl, etc.] have been reported. The structure-activity relationship (SAR) study indicated that replacement of the benzyloxy moiety in UC-112 with an indole moiety was preferred to other moieties. Among these UC-112 analogs, I (R = 5-fluoro-indol-1-ylmethyl, 5-nitro-indol-1-ylmethyl, 6-chloro-indol-1-ylmethyl, 6-methoxy-indol-1-ylmethyl) showed the most potent antiproliferative activities. Interestingly, they were more potent against the P-glycoprotein overexpressing cancer cell lines compared with the parental cancer cell lines. Mechanistic studies confirmed that new analogs maintained their unique selectivity against survivin among the IAP family members. In vivo study using I (R = 5-fluoro-indol-1-ylmethyl) in a human A375 melanoma xenograft model revealed that it effectively inhibited melanoma tumor growth without observable acute toxicity. Collectively, this study strongly supports the further preclin. development of selective survivin inhibitors based on the UC-112 scaffold. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Safety of 6-Nitro-1H-indole).

6-Nitro-1H-indole (cas: 4769-96-4) 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. 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.Safety of 6-Nitro-1H-indole

Hucher, Nicolas et al. published their research in Journal of Organic Chemistry in 2001 | 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. 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.Quality Control of 2-(Phenylthio)isoindoline-1,3-dione

蟺-Aromatic and Sulfur Nucleophilic Partners in Cationic 蟺-Cyclizations: Intramolecular Amidoalkylation and Thioamidoalkylation Cyclization via 蠅-Carbinol Lactams was written by Hucher, Nicolas;Decroix, Bernard;Daiech, Adam. And the article was included in Journal of Organic Chemistry in 2001.Quality Control of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

NaBH₄ reduction of imides followed by a 蟺-cyclization of the resultant N-acyliminium ions, generated in trifluoroacetic acid conditions, afforded two positional isomers, isoindolobenzothiazolinones. These ring closures proceeded via an intramol. 伪-amidoalkylation with the classical 蟺-aromatic or the atypical sulfur atom as an internal nucleophile. A ready access to the related six-membered N,S-heterocyclic compounds such as isoindolobenzothiazinones is also described. During this reaction, we have shown that a 蠅-carbinol lactam precursor led to endocyclic and exocyclic N-acyliminium ions in equilibrium via the a cyclic aza-sulfonium ion. The latter furnished the expected products in good yields. Similarly, different 蠅-carbinol lactams substituted at C-angular position afforded the corresponding isoindolobenzothiazinones bearing an angular alkyl, aralkyl, or aryl group. In the case of Me and benzyl groups, an addnl. amount of the dehydration products was isolated. These results indicate that the isomerization-蟺-cyclization takes place via the cleavage of the thioether linkage in acidic medium. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Quality Control of 2-(Phenylthio)isoindoline-1,3-dione).