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4-chloro-4'-hydroxy-benzophenone-(2,4-dinitro-phenylhydrazone) | 109553-61-9

中文名称
——
中文别名
——
英文名称
4-chloro-4'-hydroxy-benzophenone-(2,4-dinitro-phenylhydrazone)
英文别名
4-Chlor-4'-hydroxy-benzophenon-(2,4-dinitro-phenylhydrazon);4-[(E)-C-(4-chlorophenyl)-N-(2,4-dinitroanilino)carbonimidoyl]phenol
4-chloro-4'-hydroxy-benzophenone-(2,4-dinitro-phenylhydrazone)化学式
CAS
109553-61-9
化学式
C19H13ClN4O5
mdl
——
分子量
412.789
InChiKey
JPJQTIMJQOPDNX-QOCHGBHMSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    6.6
  • 重原子数:
    29
  • 可旋转键数:
    4
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    136
  • 氢给体数:
    2
  • 氢受体数:
    7

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    4-氯-4'-羟基二苯甲酮2,4-二硝基苯肼 在 Dowex 50W-50X2-100 cation-exchange resin 作用下, 以 甲醇 为溶剂, 反应 1.0h, 以87%的产率得到4-chloro-4'-hydroxy-benzophenone-(2,4-dinitro-phenylhydrazone)
    参考文献:
    名称:
    Design, Synthesis, and Anticancer Properties of 4,4‘-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone and Analogues
    摘要:
    4,4'-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) has recently completed a phase I clinical trial in advanced cancer with minimal toxicity, and impressive objective responses were noted. A-007 possesses three moieties that appear to have an influence on its anticancer activities: diphenylmethane, hydrazone, and dinitrophenyl. The goals of this study were to modify A-007's chemical moieties with the ultimate goal of maximizing its anticancer activity through increased planarity and introduction of functional groups. Thirty-five phenylhydrazone analogues of A-007 were synthesized and evaluated in vitro in a human primary cancer explant assay. Anticancer activities for selected analogues were also assayed for activity vs established human/murine cell lines. One-hundred-eighty-six fresh human solid tumors were used to screen for anticancer activity. Selected analogues were assayed for therapeutic indices (vs GM-CFC from bone marrow) in preparation for preclinical studies. Several polyaryl phenylhydrazones demonstrated improved cytotoxic activities by factors of 10(2)-10(3) when compared with A-007. However, the polyaryl quinone moieties of the latter analogues introduced potential toxic properties (cardiac, hematological) that do not exist with A-007.
    DOI:
    10.1021/jm0301080
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文献信息

  • [EN] CYTOTOXIC COMPOUNDS<br/>[FR] COMPOSES CYTOTOXIQUES
    申请人:MORGAN, Lee, Roy
    公开号:WO1994005276A1
    公开(公告)日:1994-03-17
    (EN) Compounds are disclosed which display cytotoxic effects against estrogen-independent tumors. These compounds may be represented by the formula X-R1 wherein X is a phenyl ring which may be substituted with one or more nitro, methyl or trihalomethyl groups and R1 is a benzophenone hydrazone, a xanthone hydrazone, a thioxanthone hydrazone, a fluoren hydrazone, an anthraquinone hydrazone, an anthraquinone phenylhydrazone, an indano [1,2,3-$i(de)]-2$i(H)-phtalazinone, a tetralin [1,2,3-$i(de)]-2$i(H)-phtalazinone, an acridone hydrazone, or a dibenzosuberenone hydrazone. The R1 moiety may be substituted with one or more hydroxy, methoxy or halogen groups. These compounds are useful as chemotherapeutic antineoplastic agents.(FR) Composés présentant des effets cytotoxiques contre des tumeurs indépendantes de l'÷strogène. Ces composés peuvent être représentés par la formule X-R1 dans laquelle X représente un cycle phényle pouvant être substitué par un ou plusieurs groupes nitro, méthyle ou trihalométhyle, et R1 représente une hydrazone de benzophénone, une hydraxone de xanthone, une hydrazone de thioxanthone, une hydrazone de fluorène, une hydrazone d'anthraquinone, une phénylhydrazone d'anthraquinone, une indano [1,2,3-$i(de)]-2$i(H)-phtalazinone, une tétraline [1,2,3-$i(de)]-2$i(H)-phtalazinone, une hydrazone d'acridone, ou une hydrazone de dibenzosubérénone. La fraction R1 peut être substituée par un ou plusieurs groupes hydroxy, méthoxy ou halogène. Ces composés sont utiles en tant qu'agents chimiothérapeutiques antinéoplasiques.
  • [EN] SALT COMPLEX FOR LYMPHATIC DELIVERY<br/>[FR] COMPLEXE DE SELS ADMINISTRE AU SYSTEME LYMPHATIQUE
    申请人:DEKK-TEC, INC.
    公开号:WO1998058649A1
    公开(公告)日:1998-12-30
    (EN) Compounds and methods are disclosed for directed delivery of antineoplastic drugs to the lymphatic system, which often harbors metastatic disease that is difficult to treat with conventional chemotherapy. The antineoplastic drugs form salts with lymphangitic substances, such as lymphangitic dyes, which are chemotrophic for lymphatic vessels. In particular embodiments, antineoplastic hydrazones, such as 4,4'-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007), form multiple salts (such as double salts) and complexes with heterocyclic and polyaromatic amines and sulfonic acid dyes, such as methylene blue (MB) and gentian violet (GV). The cytotoxic properties of the hydrazone compounds are potentiated by a log-fold increase in activity when the molecule is bound through electrostatic bonds to lymphangitic dyes. Directed delivery of the drugs to the lymphatic system helps treat micrometastatic disease that is present in the lymphatic system. The lymphangitic salts can be administered either systemically or locally. Local administration can include topical and intradermal administration in a solvent that promotes movement of the drug complex through the dermis and into the lymphatic vessels.(FR) L'invention concerne des composés et procédés permettant d'administrer de manière dirigée des médicaments antinéoplasiques au système lymphatique qui héberge souvent une maladie métastatique difficile à traiter au moyen d'une chimiothérapie classique. Les médicaments antinéoplasiques forment des sels contenant des substances permettant d'identifier une lymphangite, telles que des colorants, substances qui ont une action chémotrophe à l'égard des vaisseaux lymphatiques. Selon des modes de réalisation particuliers, les hydrazones antinéoplasiques, telles que la 4,4'-dihydroxybenzophénone-2,4-dinitrophénylhydrazone (A-007), forment des sels multiples (tels que des sels doubles) et des complexes avec des amines hétérocycliques et polyaromatiques ainsi qu'avec des colorants à base d'acide sulfonique, tels que le bleu de méthylène (MB) et le violet de gentiane (GV). Les propriétés cytotoxiques des composés d'hydrazone sont potentialisées par une croissance logarithmique de leur activité lorsque la molécule est liée, au moyen de liaisons électrostatiques, aux colorants permettant d'identifier une lymphangite. L'administration dirigée de ces médicaments au système lymphatique aide à traiter la maladie micrométastasique présente dans le système lymphatique. Les sels permettant d'identifier la lymphangite peuvent être administrés soit par la voie systémique, soit par la voie locale. L'administration locale peut inclure les administrations topique et intradermale dans un solvant qui accélère la progression du complexe médicamenteux à travers le derme et dans les vaisseaux lymphatiques.
  • Design, Synthesis, and Anticancer Properties of 4,4‘-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone and Analogues
    作者:Lee Roy Morgan、Kanappan Thangaraj、Blaise LeBlanc、Andrew Rodgers、Lionel T. Wolford、Catherine L. Hooper、Dominic Fan、Branko S. Jursic
    DOI:10.1021/jm0301080
    日期:2003.10.1
    4,4'-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) has recently completed a phase I clinical trial in advanced cancer with minimal toxicity, and impressive objective responses were noted. A-007 possesses three moieties that appear to have an influence on its anticancer activities: diphenylmethane, hydrazone, and dinitrophenyl. The goals of this study were to modify A-007's chemical moieties with the ultimate goal of maximizing its anticancer activity through increased planarity and introduction of functional groups. Thirty-five phenylhydrazone analogues of A-007 were synthesized and evaluated in vitro in a human primary cancer explant assay. Anticancer activities for selected analogues were also assayed for activity vs established human/murine cell lines. One-hundred-eighty-six fresh human solid tumors were used to screen for anticancer activity. Selected analogues were assayed for therapeutic indices (vs GM-CFC from bone marrow) in preparation for preclinical studies. Several polyaryl phenylhydrazones demonstrated improved cytotoxic activities by factors of 10(2)-10(3) when compared with A-007. However, the polyaryl quinone moieties of the latter analogues introduced potential toxic properties (cardiac, hematological) that do not exist with A-007.
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