68027-22-5

Usage

Uses

Used in Scientific Research:
(2-aminoethyl)guanidine dihydrochloride is used as a pharmacological tool for studying the functions and mechanisms of action of guanidine compounds, aiding in the understanding of their role in various physiological and pathological processes.
Used in Pharmaceutical Development:
AEG-1 is used as a potential therapeutic agent for the treatment of neurological and autoimmune diseases, leveraging its demonstrated effects in these areas to develop new treatment options.
Used in Oncology Research:
(2-aminoethyl)guanidine dihydrochloride is used as an agent for studying its anti-tumor properties, exploring its potential to contribute to cancer treatment and management.
Used in Inflammation Studies:
AEG-1 is used as an anti-inflammatory agent in research, examining its effects on inflammatory processes to potentially develop treatments for inflammatory conditions.
Used in Neurotransmitter Regulation Research:
(2-aminoethyl)guanidine dihydrochloride is used to study neurotransmitter function and regulation due to its ability to modulate neurotransmitter release in the brain, providing insights into neurological disorders and their treatments.

InChI:InChI=1/C3H10N4.2ClH/c4-1-2-7-3(5)6;;/h1-2,4H2,(H4,5,6,7);2*1H

Upstream product

• 77152-92-2 N-<2-<(tert-butoxycarbonyl)amino>ethyl>guanidine 
• 107-15-3 ethylenediamine 
• 194483-89-1 N-BOC-2-aminoethylguanidine hydroiodide 
• 79513-35-2 N-(tert-butyloxycarbonyl)-1,2-ethanediamine hydrochloride 
• 4023-02-3 1H-pyrazole-1-carboximidamide hydrochloride 

Relevant academic research and scientific papers

The discovery of a new potential anticancer drug: A case history

DNA minor groove binders (MGB) represent a class of anticancer agents whose DNA sequence specificity was hypothesized to lead to high selectivity of action. Tallimustine (TAM), a benzoyl nitrogen mustard derivative of distamycin A (DST), showed excellent antitumor activity in preclinical tests, but also a severe myelotoxicity. Novel nitrogen mustard, nitrogen half-mustard and sulfur mustard derivatives of DST showing excellent activity were recently identified and SAR reported. In particular nitrogen half-mustard and sulfur mustard derivatives, as one-arm alkylating agents, represent interesting structural novelties. A further new class of cytotoxic anticancer agents is that of α-halogenoacrylamido derivatives of DST-like oligopeptides, which show an activity profile substantially improved in comparison to TAM. In particular brostallicin (PNU-166196), α-bromo-acrylamido tetra-pyrrole derivative ending with a guanidino moiety, showed high cytotoxic potency and myelotoxicity dramatically reduced in comparison to TAM and other MGB. Brostallicin binds to the minor groove but appears unreactive in classical in vitro DNA alkylation assays. About the apparent lack of DNA alkylation we speculated that an intracellular nucleophile, e.g. glutathione (GSH), could activate the reactivity of the compound leading to alkylation of DNA in vivo. Evidence of both covalent interaction of brostallicin with plasmidic DNA in the presence of GSH and of enhanced cytotoxicity in cancer cells characterized by high levels of GSH were obtained. Brostallicin was selected for clinical development and is now undergoing Phase II studies.

Discovery of Amphamide, a Drug Candidate for the Second Generation of Polyene Antibiotics

Amphotericin B (AmB, 1) is the drug of choice for treating the most serious systemic fungal or protozoan infections. Nevertheless, its application is limited by low solubility in aqueous media and serious side effects such as infusion-related reactions, hemolytic toxicity, and nephrotoxicity. Owing to these limitations, it is essential to search for the polyene derivatives with better chemotherapeutic properties. With the objective of obtaining AmB derivatives with lower self-aggregation and improved solubility, we synthesized a series of amides of AmB bearing an additional basic group in the introduced residue. The screening of antifungal activity in vitro revealed that N-(2-aminoethyl)amide of AmB (amphamide, 6) had superior antifungal activity compared to that of the paternal AmB. Preclinical studies in mice confirmed that compound 6 had a much lower acute toxicity and higher antifungal efficacy in the model of mice candidosis sepsis compared with that of AmB (1). Thus, the discovered amphamide is a promising drug candidate for the second generation of polyene antibiotics and is also prospective for in-depth preclinical and clinical evaluation.

Trialkoxysilanes connected with thioether bond on alpha-carbon and containing different functional groups based on sulfydryl-ene click reaction, and preparation

The invention relates to a preparation method of trialkoxysilanes connected with a thioether bond on alpha-carbon and containing different functional groups. The method comprises the steps of reactingchloromethyltrichlorosilane and sodium alkoxide so as to prepare chloromethyltriethoxysilane, then reacting chloromethyltriethoxysilane and thiourea under the action of a catalyst so as to prepare alpha-sulfydrylmethyltriethoxysilane; through performing photo-initiation sulfydryl-ene click reaction, connecting alpha-sulfydrylmethyltriethoxysilane and a double-bond compound, and thus obtaining trialkoxysilanes connected with the thioether bond on the alpha-carbon and containing the different functional groups. According to the method, one of the raw materials is the industrial byproduct chloromethyltrichlorosilane, and the efficient utilization way is opened for chloromethyltrichlorosilane, so that environment protection and energy conversation are realized, the dosage of a toxic catalystis reduced, and the idea of green environment protection is met. According to the preparation method provided by the invention, the raw materials and reaction reagents are easy to get, the product iseasy to separate and purify, and the atom economy is met; the preparation process is simple, the reaction condition is mild, the cost is low, and the preparation method is suitable for large-scale industrial production and application.

Using N-substituted-2-amino-4,6-dimethoxypyrimidines in the synthesis of aliphatic guanidines

Abstract The use of 2-chloro-4,6-dimethoxypyrimdine as a tool for the syntheses of substituted guanidines is presented. This method, that we had previously shown to be very useful for aromatic amines, introduces an atom economical, cost effective and environmentally safe method for the installation of the guanidine functionality in aliphatic primary and secondary amines.

Process for preparing distamycin derivatives

It is described a process for preparing, in high yields and purity and without the need of carrying out several steps and/or isolating many intermediates which could lead to undesired by-products, a distamycin derivative of formula wherein R is a bromine or chlorine atom; or a pharmaceutically acceptable salt thereof. The compounds of formula (I) are useful in therapy as antitumor agents.

Acryloyl derivatives analogous to distamycin, process for preparing them, and their use as antitumor agents

Compounds which are acryloyl substituted distamycin derivatives of formula (I) wherein: n is 2, 3 or 4; m is 1 or 2; X and Y are the same or different and are selected, independently for each heterocyclic ring of the polyetherocyclic chain, from N and CH; R1and R2, which are the same or different, are selected from hydrogen, halogen, and C1-C4alkyl; R3is hydrogen or halogen; B is selected from (a), (b), (c), (d), (e), (f), (g) and —C≡N; wherein R4, R5, R6, R7, R8, R10, R11, and R12are, independently from each other, hydrogen or C1-C4alkyl; and R9is hydrogen or hydroxy, or pharmaceutically acceptable salt thereof; provided that a) at least one of R4, R5and R6is alkyl b) at least one of the heterocyclic rings within the polyheterocyclic chain is other than pyrole; and c) X and Y are not both N for the same heterocyclic ring; are useful as antitumor agents.

Cytotoxic α-Halogenoacrylic Derivatives of Distamycin A and Congeners

The mechanism of action of many antitumor agents involves DNA damage, either by direct binding of the drug to DNA or to DNA-binding proteins. However, most of the DNA-interacting agents have only a limited degree of sequence specificity, which implies that they may hit all the cellular genes. DNA minor groove binders, among which the derivatives of distamycin A play an important role, could provide significant improvement in cancer management, increasing gene specificity, due to high selectivity of interaction with thymine-adenine (TA) rich sequences. We now report and discuss the synthesis, the in vitro and in vivo activities, and some mechanistic features of α-halogenoacrylamido derivatives of distamycin A. The final result of this work was the selection of brostallicin 17 (PNU-166196). Brostallicin, presently in phase II clinical trials, shows a broad spectrum of antitumor activity and an apoptotic effect higher than distamycin derivative tallimustine. An important in vitro toxicological feature of brostallicin is the very good ratio between myelotoxicity on human haematopoietic progenitor cells and cytotoxicity on tumor cells, in comparison with clinically tested DNA minor groove binders. A peculiarity of brostallicin is its in vitro reactivity in the DNA alkylation assays only in the presence of glutathione. Moreover brostallicin's antitumor activity, both in in vitro and in vivo tumor models, is higher in the presence of increased levels of glutathione/glutathione-S-tranferases. These findings contribute to the definition of brostallicin as a novel anticancer agent that differs from other minor groove binders and alkylating agents for both the profile of activity and the mechanism of action and to. classify the α-bromoacrylamido derivatives of distamycin as a new class of cytotoxics. Moreover, due to its interaction with glutathione, brostallicin may have a role for the tailored treatment of tumors characterized by constitutive or therapy-induced overexpression of glutathione/glutathione-S-tranferase levels.

Benzoheterocyclic distamycin derivatives, process for preparing them, and their use as antitumor agents

Compounds which are benzoheterocyclic distamycin derivatives of formula (I), wherein n is 2, 3 or 4; A is a heteroatom selected from O and S or is a group NR, wherein R is hydrogen or C1-C4alkyl; B is CH or N; R1is hydrogen or C1-C4alkyl; G is selected from the group consisting of (a, b, c, d, e, f, g, h, i, j), and —C≡N; wherein R5, R6, R7, R8, R9, R10, R11and R12are, independently from each other, hydrogen or C1-C4alkyl; T is a group of formula (II) or (III) as defined above, wherein p is 0 or 1; R2and R3are, independently from each other, hydrogen, C1-C4alkyl optionally substituted by one or more fluorine atoms, or C1-C4alkoxy; R4is C1-C4alkyl or C1-C3haloalkyl; X1and X2are halogen atoms or pharmaceutically acceptable salts thereof; provided that at least one of R5, R6and R7is alkyl; are useful as antitumor agents.

Acryloyl substituted distamycin derivatives, process for preparing them, and their use as antitumor and antiviral agents

The present invention relates to acrylol substituted distamycin derivatives, to pharmaceutical compositions comprising such derivatives as well as their use in methods of treating humans and animals, particularly as anti-tumor agents.