88457-23-2

Basic information

• Product Name: methyl 4-[bis(2-chloroethyl)amino]-L-phenylalaninate
• Synonyms: melphalanmethylester;Melphalan EP impurity H;Melphalan Methyl Ester Impurity;Melphalan EP Impurity H (Melphalan Methyl Ester);L-Phenylalanine, 4-[bis(2-chloroethyl)amino]-, methyl ester;Melphalan EP Impurity HQ: What is Melphalan EP Impurity H Q: What is the CAS Number of Melphalan EP Impurity H Q: What is the storage condition of Melphalan EP Impurity H Q: What are the applications of Melphalan EP Impurity H
• CAS NO: 88457-23-2
• Molecular Formula: C₁₄H₂₀Cl₂N₂O₂
• Molecular Weight: 319.2268
• Mol File: 88457-23-2.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 437.6°C at 760 mmHg
• Flash Point: 218.5°C
• Density: 1.244g/cm³
• Vapor Pressure: 7.36E-08mmHg at 25°C
• Refractive Index: 1.565
• PKA: 7.70±0.33(Predicted)
• CAS DataBase Reference: methyl 4-[bis(2-chloroethyl)amino]-L-phenylalaninate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-[bis(2-chloroethyl)amino]-L-phenylalaninate(88457-23-2)
• EPA Substance Registry System: methyl 4-[bis(2-chloroethyl)amino]-L-phenylalaninate(88457-23-2)

Safety Data

• Hazardous Substances Data: 88457-23-2(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 148-82-3 L-PAM 
• 265645-66-7 (S)-3-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-2-[3-methyl-3-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-butyrylamino]-propionic acid methyl ester 
• 265645-64-5 (S)-3-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-2-[3-(5-bromo-2,4-dimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-3-methyl-butyrylamino]-propionic acid methyl ester 
• 265645-65-6 (S)-3-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-2-[3-(2,4-dimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-3-methyl-butyrylamino]-propionic acid methyl ester 

Relevant articles and documents

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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.