830-94-4

Usage

Uses

Used in Antimalarial Applications:
5-Chloro-gramine is used as an antimalarial agent due to its potential activity against malaria-causing parasites, as observed in in vitro studies.
Used in Cancer Treatment:
In the field of oncology, 5-Chloro-gramine is used as a cytotoxic agent for its potential to target and eliminate cancer cells, offering a novel approach to cancer treatment.
Used in Antibacterial Applications:
5-Chloro-gramine is utilized as an antibacterial agent, particularly against drug-resistant bacteria, showcasing its potential to combat antibiotic resistance.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 5-Chloro-gramine serves as a subject of research for its pharmacological effects and possible therapeutic uses, with the aim of developing new treatments for various diseases.

Upstream product

• 17422-32-1 5-chloro-1H-indole 
• 33797-51-2 eschenmoser's salt 
• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 
• 506-59-2 N,N-dimethylammonium chloride 

Downstream Products

• 936366-47-1 C₂₂H₂₂ClF₂N₂O₃P 
• 154-07-4 2-amino-3-(5-chloro-1H-indol-3-yl)propanoic acid 
• 81630-83-3 2-(5-chloro-1H-indol-3-yl)acetonitrile 

Relevant academic research and scientific papers

Substitution of the Dimethylamino Group in Gramines and One-Pot Cyclization to Tetrahydro-β-carbolines Using a Triazine-Based Activating Agent

A new method for the substitution of 3-[(dimethylamino)methyl]indoles (gramines) with malonate-based nucleophiles was developed using 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) as the activating agent for the dimethylamino group. The reaction was completed in 1.5-6 h at room temperature in the presence of a tert-amine base and lithium salt. CDMT afforded superior results to methyl iodide, a common activating agent for the dimethylamino group in Mannich bases, particularly in the reactions of 1-substituted gramines. The reactivity of the possible intermediates, bis(indol-3-ylmethyl)dimethylammonium salts, was examined to obtain mechanistic insights on the reaction. This substitution method with CDMT enabled the sequential transformation of gramines: substitution with (N-alkylidene)aminomalonates followed by the Pictet-Spengler reaction under acidic conditions afforded 1,2,3,4-tetrahydro-β-carboline derivatives in one pot.

Rhodium-Catalyzed Enantioselective Cyclization of 3-Allenyl-indoles: Access to Functionalized Tetrahydrocarbazoles

A highly selective rhodium-catalyzed cyclization of tethered 3-allenylindoles is reported. In a smooth reaction, 1-vinyltetrahydrocarbazoles are obtained in excellent yields and enantioselectivities. Aside from a great functional group tolerance, this method requires neither the Schlenk technique nor the use of anhydrous solvents. Preliminary mechanistic investigations proved that the reaction proceeds via an intermediary formed spiroindolenine which rapidly undergoes an acid-catalyzed stereospecific migration.

Rhodium-Catalyzed Diastereo- And Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines

A highly selective rhodium-catalyzed tandem spirocyclization/reduction of 3-allenylindoles is reported. By employing a Hantzsch ester as reductant, vinylic spiroindolines are obtained in excellent yields as well as diastereo- and enantioselectivity. In addition, the reaction's synthetic utility is highlighted by broad functional group compatibility and exemplified by a gram scale reaction with subsequent assorted transformations.

INDOLOPYRIDINES AS INHIBITORS OF THE KINESIN SPINDLE PROTEIN (EG5 )

Compounds of formula (I), in which R1, R2, R3 and R4 have the meanings indicated in the description, are effective Eg5-inhibiting compounds with anti-proliferative and/or apoptosis inducing activity.

TETRACYCLIC INDOLOPYRIDINES AS EG5 INHIBITORS

Compounds of a certain formula (I), in which R1, R2, R3 and R4 have the meanings indicated in the description, are effective Eg5-inhibiting compounds with anti-proliferative and/or apoptosis inducing activity.

Enantioselective gold-catalyzed allylic alkylation of indoles with ALcohols: An efficient route to functionalized tetrahydrocarbazoles

[Chemical equation presented] Breaking the taboo: The direct use of allylic alcohols in catalytic and enantioselective Friedel-Crafts alkylation is described for the first time In the presence of chiral gold complexes. This intramolecular Friedel-Crafts reaction was used to prepare a broad range of functionalized tetrahydrocarbazoles (see scheme; X=Me, F, Br, Cl, OMe; R=Me, Et, tBu; R′=H, Me).

Discovery of potent, selective, orally active, nonpeptide inhibitors of human mast cell chymase

A series of β-carboxamido-phosphon(in)ic acids (2) was identified as a new structural motif for obtaining potent inhibitors of human mast cell chymase. For example, 1-naphthyl derivative 5f had an IC50 value of 29 nM and (E)-styryl derivative 6

INDOLOPYRIDINES AS EG5 KINESIN MODULATORS

Compounds of a certain formula (I), in which R1, R2, R3, R4, R5 and R6 have the meanings indicated in the description, are effective compounds with anti-proliferative and/or apoptosis inducing activity.

N-ARYLOXYALKYL TRYPTAMINE ALPHA1-ADRENERGIC RECEPTOR ANTAGONISTS

The present invention relates to novel N-aryloxyalkyl tryptamine . alpha. 1-adrenergic receptor antagonists of the formula I: STR1 in which n is 2, 3 or 4; q is 1, 2 or 3; t is 0, 1, 2 or 3; z is 0, 1, 2 or 3; each R 1 and R 2 are independently hydroxy, halogen, cyano, (C 1-8)alkyl, (C 1-8)alkyloxy or trifluoromethyl; and R 2 is hydrogen, (C 1-4)alkyl, fluoro(C 1-4)alkyl, difluoro(C 1-4) alkyl, trifluoro(C 1-4)alkyl, (C 1-4) alkyloxy(C 1-4)alkyl, oxo(C 1-4)alkyl, (C 1-8)cycloalkyl, (C. sub.1-8)cycloalkylmethyl or allyl or phenyl(C 1-4)alkyl or heterocyclo(C 1-8)alkyl (optionally substituted with one to two substituents independently selected from (C 1-4)alkyl, (C 1-4) alkyloxy, trifluoromethyl and halogen); R. sup.3 and R 4 are independently hydrogen, (C 1-4) alkyl, (C 1-8)cycloalkyl, (C 1-8)cycloalkylmethyl or allyl; and R. sup. 5 is hydrogen, (C 1-4)alkyl, (C 1-8)cycloalkyl, (C 1-8) cycloalkylmethyl, allyl, (C 1-4) alkylsulfonyl and aminocarbonyl; with the proviso that when n is 2, t is 0, q is 1, z is 0, 1 or 2, R 5 is hydrogen and R 6 is hydroxy or (C 1-8)alkyloxy then at least one of R 3 and R 4 is not hydrogen; and the pharmaceutically acceptable salts, individual isomers, and mixtures of isomers thereof; their uses as therapeutic agents and the methods of their making.

N-Substituted-2-(1-imidazolyl)indoles

Various 1-carboxylic acid substituted-2-(1-imidazolyl)indoles and functional derivatives thereof are highly specific thromboxane synthetase inhibitors. Synthesis of, pharmaceutical compositions thereof, methods of treatment utilizing such compounds and intermediates for their synthesis are included.