15716-30-0

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InChI:InChI=1/C13H19NO4/c1-2-18-13(17)11-3-5-12(6-4-11)14(7-9-15)8-10-16/h3-6,15-16H,2,7-10H2,1H3

Upstream product

• 75-21-8 oxirane 
• 94-09-7 p-aminoethylbenzoate 
• 99-77-4 ethyl 4-nitrobenzoate 
• 62-23-7 4-nitro-benzoic acid 
• 107-07-3 2-chloro-ethanol 
• 150-13-0 4-amino-benzoic acid 

Relevant academic research and scientific papers

Design and synthesis of chromone-nitrogen mustard derivatives and evaluation of anti-breast cancer activity

Chromone has emerged as one of the most important synthetic scaffolds for antitumor activity, which promotes the development of candidate drugs with better activity. In this study, a series of nitrogen mustard derivatives of chromone were designed and syn

Novel diosgenin–amino acid–benzoic acid mustard trihybrids exert antitumor effects via cell cycle arrest and apoptosis

In discovering new powerful antitumor agents, two series of novel diosgenin–amino acid–benzoic acid mustard trihybrids (7a–7 g and 12a–12 g) were designed and synthesized. The antiproliferative activities were tested against five human tumor cell lines an

Design and synthesis of β-carboline derivatives with nitrogen mustard moieties against breast cancer

To discover the promising antitumor agents, a series of β-carboline derivatives with nitrogen mustard moieties were designed and synthesized. Most target derivatives showed antiproliferative activity against MCF-7 and MDA-MB-231 cells. Among them, (1-meth

A class β . Preparation method and anti-tumor application

The invention discloses β -carbofuran mustard derivatives as well as a preparation method and application thereof, and belongs to the field of natural medicines and medicinal chemistry. The invention specifically relates to a preparation method of a serie

Benzoic acid nitrogen mustard fragment-containing compound and preparation method and use thereof

The invention relates to the field of natural medicine and medicine chemistry, and particularly relates to a compound containing benzoic acid nitrogen mustard fragment and a preparation process and use, in particular to a compound which introduces a benzoic acid nitrogen mustard fragment at a 4'-OH through a linking group after derivatization of the 6, 7-position of scutellarin, and a pharmaceutically acceptable salt thereof. The method also relates to the preparation process and antitumor activity of these compounds. The method of the benzoic acid nitrogen mustard fragment-containing compoundis shown in the general formula I, wherein m, n are as described in the claims and the specification. The formula is shown in the description.

Novel enmein-type diterpenoid hybrids coupled with nitrogen mustards: Synthesis of promising candidates for anticancer therapeutics

Natural derived enmein-type diterpenoids exert cytotoxicity against a wide range of human cancer cells. Yet their medicinal applications are hindered by insufficient potency for chemotherapy. Hence, a series of novel enmein-type diterpenoid hybrids coupled with nitrogen mustards were designed and synthesized to increase antitumor efficacy while reducing systemic toxicity. Most conjugates exhibited stronger antiproliferative activities than parent diterpenoids and nitrogen mustards, especially for multidrug-resistant tumor cell line Bel-7402/5-FU. Among them, compound E2 showed the most potent inhibitory activities in human leukemia HL-60 cells, human prostate cancer PC-3 cells, human liver cancer Bel-7402 cells and drug-resistant human liver cancer Bel-7402/5-FU cells with IC50 values of 7.83 μM, 3.97 μM, 0.77 μM and 2.07 μM, respectively. Additionally, high selectivity with selectivity index over 130 was also observed from cytotoxic evaluation between L-02 human normal liver cells and Bel-7402 malignant liver cells. Further studies on mechanism of action indicated that E2 induced both apoptosis and G1 phase cell cycle arrest in Bel-7402 hepatoma cells. Moreover, the dysfunction in mitochondrial pathway was also involved in E2 initiated apoptotic activation, which entailed the loss of mitochondrial membrane potential followed by upregulating the bax/bcl-2 ratio and increasing the expression of cytochrome c, p53, caspase-3 and -9. Overall, E2 has the potential to emerge as a promising drug candidate for cancer therapy.

Improving the Potency of Cancer Immunotherapy by Dual Targeting of IDO1 and DNA

Herein we report the first exploration of a dual-targeting drug design strategy to improve the efficacy of small-molecule cancer immunotherapy. New hybrids of indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors and DNA alkylating nitrogen mustards that respectively target IDO1 and DNA were rationally designed. As the first-in-class examples of such molecules, they were found to exhibit significantly enhanced anticancer activity in vitro and in vivo with low toxicity. This proof-of-concept study has established a critical step toward the development of a novel and effective immunotherapy for the treatment of cancers.

Novel hybrids of brefeldin A and nitrogen mustards with improved antiproliferative selectivity: Design, synthesis and antitumor biological evaluation

A series of novel conjugates of brefeldin A (11a?c, 12a?c and 13a?c) were obtained by introducing a variety of nitrogen mustards at 4-OH or 7-OH position to explore more efficacious and less toxic antitumor agents. The antiproliferative activities were te

Synthesis of scutellarein derivatives with antiproliferative activity and selectivity through the intrinsic pathway

To explore antitumor agents with potent efficacy and low toxicity, scutellarein derivatives with benzoic acid mustard (10a?c, 11a?c and 13a?c) were designed and synthesized. The antiproliferative activities of the target derivatives against A549, MCF-7 and Bel-7402 cancer cell lines were tested. Compound 10a showed the strongest potency with an IC50 value of 1.50 μM against MCF-7 cell line, and displayed low toxicity against human liver L-O2 normal cells (IC50 > 50 μM), showing specificity between normal and malignant cells. The mechanism studies revealed that 10a could induce apoptosis in MCF-7 cells, arrest MCF-7 cell cycle at the G1 phase and cause mitochondrial dysfunction in a concentration-dependant manner. Furthermore, the enhanced expression of the pro-apoptotic proteins caspase-9, caspase-3, Bax and cytochrome c, and the reduced expression of the anti-apoptotic protein Bcl-2 confirmed that 10a induced the intrinsic apoptosis pathway in MCF-7 cells. The potent antiproliferative activity and good selectivity guaranteed 10a a lead compound for the further development into anticancer therapeutics, especially for breast cancer.

Design and synthesis of novel nitrogen mustard-evodiamine hybrids with selective antiproliferative activity

A series of novel nitrogen mustard-evodiamine hybrids were synthesized and evaluated for their antitproliferative properties. The antiproliferative activities of 10a–d, 11a–d, and 12a–d against four different kinds of human cancer cell lines (PC-3, HepG2, THP-1 and HL-60) and human normal peripheral blood mononuclear cells (PBMC) were determined. The results showed that all the target hybrid compounds exhibited antiproliferative activities against tested human tumor cell lines to some extent and no antiproliferative activities (>200 μM) against human normal PBMC cells. The antiproliferative selectivity between tumorous and normal cells was very useful for further antitumor drug development. Among the target compounds, 12c showed the strongest cytotoxicity against two tumor cell lines (THP-1 and HL-60) with IC50 values of 4.05 μM and 0.50 μM, respectively, and selected for further mechanism study in HL-60 cells. The results showed that 12c could induce HL-60 cells apoptosis and arrest at G2 phase at low sub-micromolar concentrations via mitochondria-related pathways.