136818-66-1 | - Indole Building Blocks

Lavrenov, Sergei N.’s team published research in Synthesis in 2002-02-28 | CAS: 136818-66-1

Synthesis published new progress about methyl nitro indole carboxylate nitration; indoline carboxylic acid methyl ester nitro preparation. 136818-66-1 belongs to class indole-building-block, name is Methyl 6-nitro-1H-indole-2-carboxylate, and the molecular formula is C10H8N2O4, COA of Formula: C10H8N2O4.

Lavrenov, Sergei N. published the artcileSynthesis of methyl 5- and 6-nitroindole-2-carboxylates by nitration of indoline-2-carboxylic acid, COA of Formula: C10H8N2O4, the main research area is methyl nitro indole carboxylate nitration; indoline carboxylic acid methyl ester nitro preparation.

Indoline-2-carboxylic acid was transformed into 6-nitroindoline-2-carboxylic acid, the Me ester of which was easily dehydrogenated by DDQ to Me 6-nitroindole-2-carboxylate (total yield: 67%). Me 5-nitroindole-2-carboxylate was obtained by the nitration of Me 1-acetylindoline-2-carboxylate acid followed by dehydrogenation with MnO2 in toluene in 40% total yield.

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

Ranasinghe, Nadeesha’s team published research in Bioorganic & Medicinal Chemistry Letters in 2013-03-15 | CAS: 136818-66-1

Bioorganic & Medicinal Chemistry Letters published new progress about [3+2] Cycloaddition reaction. 136818-66-1 belongs to class indole-building-block, name is Methyl 6-nitro-1H-indole-2-carboxylate, and the molecular formula is C10H8N2O4, Safety of Methyl 6-nitro-1H-indole-2-carboxylate.

Ranasinghe, Nadeesha published the artcileExtending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry, Safety of Methyl 6-nitro-1H-indole-2-carboxylate, the main research area is Hemetsberger Knittel indole synthesis microwave chem.

Microwave, flow and combination methodologies were applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodol. allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chem., allowing formation of peptide adducts which can be subsequently labeled with fluorine tags.

Nishiyama, Takashi’s team published research in European Journal of Medicinal Chemistry in 2016-10-04 | CAS: 136818-66-1

European Journal of Medicinal Chemistry published new progress about Antiproliferative agents. 136818-66-1 belongs to class indole-building-block, name is Methyl 6-nitro-1H-indole-2-carboxylate, and the molecular formula is C10H8N2O4, Application In Synthesis of 136818-66-1.

Nishiyama, Takashi published the artcileConcise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells, Application In Synthesis of 136818-66-1, the main research area is carbazolequinone preparation antiproliferative human; indole allyl alc tandem ring closing metathesis dehydrogenation; Antiproliferative activity; Carbazole-1,4-quinone; Koeniginequinone A; Koeniginequinone B.

A convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step is reported. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions I (R1 = R2 = H, CH3; R3 = H, 6-OCH3, 5,6-(OCH3)2, 7-CH3, 6-NO2, etc.; R4 = H, MOM) have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.

Boger, Dale L.’s team published research in Bioorganic & Medicinal Chemistry in 1995-06-30 | CAS: 136818-66-1

Bioorganic & Medicinal Chemistry published new progress about Biochemical alkylation. 136818-66-1 belongs to class indole-building-block, name is Methyl 6-nitro-1H-indole-2-carboxylate, and the molecular formula is C10H8N2O4, Category: indole-building-block.

Boger, Dale L. published the artcileCC-1065 CBI analogs: an example of enhancement of DNA alkylation efficiency through introduction of stabilizing electrostatic interactions, Category: indole-building-block, the main research area is CC1065 CBI analog preparation DNA alkylation.

The three trimethylammonium salts I (R1 and R2 and R3 = H or NMe3+) proved to be 100 times more efficient at alkylating DNA than I (R1 and R2 and R3 = H) and exhibited DNA alkylation efficiencies identical to that of (+)-CC-1065. In addition, the agents I (R1 and R2 = H and R3 = NMe3+) and I (R1 and R3 = H and R2 = NMe3+) exhibited DNA alkylation selectivities identical to that of I (R1 and R2 and R3 = H). This may be attributed to spatially well-defined stabilizing electrostatic interactions between the pos. charged trimethylammonium salt lying on the peripheral face of the agents and the bracketing, neg. charged phosphates located in the DNA backbone that enhance the DNA noncovalent binding affinity without affecting DNA binding or alkylation selectivity. The agent I (R2 and R3 = H and R1 = NMe3+) exhibited an altered and more discriminating AT-rich adenine N3 alkylation selectivity than the other agents that may be attributed to the groove placement of the large trimethylammonium salt.