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Synthesis and Biological Evaluation of 1,1-Dichloro-2,3-Diarylcyclopropanes As Antitubulin and Anti-Breast Cancer Agents

  1. Author:
    Jonnalagadda, S. S.
    Terhaar, E.
    Hamel, E.
    Lin, C. M.
    Magarian, R. A.
    Day, B. W.

  2. Author Address

    Day BW UNIV PITTSBURGH DEPT ENVIRONM & OCCUPAT HLTH 260 KAPPA DR PITTSBURGH, PA 15238 USA UNIV PITTSBURGH DEPT ENVIRONM & OCCUPAT HLTH PITTSBURGH, PA 15238 USA UNIV PITTSBURGH DEPT PHARMACEUT SCI PITTSBURGH, PA 15238 USA UNIV PITTSBURGH INST CANC PITTSBURGH, PA 15238 USA NCI FREDERICK CANC RES & DEV CTR LAB DRUG DISCOVERY RES & DEV DIV CANC TREATMENT DIAGNOSIS & CTR FREDERICK, MD 21702 USA UNIV OKLAHOMA HLTH SCI CTR DEPT MED CHEM & PHARMACEUT OKLAHOMA CITY, OK 73190 USA
    1. Year: 1997
  2. Journal: Bioorganic & Medicinal Chemistry
    1. 5
    2. 4
    3. Pages: 715-722
  4. Type of Article: Article
  1. Abstract:

    Z-1,1-Dichloro-2,3-diphenylcyclopropane (1) is an effective 'anti-breast cancer agent in rodents and in cell culture. We recently determined that 1 inhibits tubulin assembly in vitro. and causes microtubule loss in breast cancer cells, leading to accumulation in the G2/M portion of the cell cycle. Aryl ring-halogenated, methoxylated and benzyloxylated derivatives of 1, as well as its E-isomer and the dichlorocyclopropyl derivative of diethylstilbestrol (DES), were synthesized and tested for their ability to inhibit the assembly of tubulin into micro tubules. Including 1, 17 cyclopropyl compounds were tested. One (Z-1,1-dichloro-2-(4-methoxyphenyl)-3-phenylcyclopropane (12)) was found to be more active than 1. In addition, E-1,1-dichlorocyclopropylDES (17) was more potent than DES. The E-isomer of 1 (16) was inactive. The cytostatic activities of the compounds against MCF-7 and MDA-MB231 human breast cancer cells, and their abilities to perturb microtubules in MCF-7 cells were also evaluated. Z-Dichloro-2-(4-fluorophenyl)-3-phenylcyclo (5), Z-1,1-dichloro-2-(4-fluorophenyl)-3-(4-methoxyphenyl)cyclopropane (11), and Z-1,1-dichloro-2-(4-methoxyphenyl) -3-phenylcyclopropane (12) were more potent than 1 against the breast cancer cells. (C) 1997 Elsevier Science Ltd. [References: 17]

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