2-<(tert-butylphenyl)amino>-6-chloro-3-nitrobenzoic acid | 166756-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-<(tert-butylphenyl)amino>-6-chloro-3-nitrobenzoic acid
• 英文别名: 2-[(4-tert-Butylphenyl)amino]-6-chloro-3-nitrobenzoic acid；2-(4-tert-butylanilino)-6-chloro-3-nitrobenzoic acid
• CAS: 166756-48-5
• 化学式: C₁₇H₁₇ClN₂O₄
• 分子量: 348.786
• InChiKey: CUJRDZMOCYDZJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<(tert-butylphenyl)amino>-6-chloro-3-nitrobenzoic acid 在 三乙胺 、 三氯氧磷 作用下， 以 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 10.5h， 生成 7-tert-butyl-4-nitro-1-<<3-propyl>amino>propyl>amino>-9(10H)-acridinone
  参考文献：
  名称：

  Bisimidazoacridones and Related Compounds: New Antineoplastic Agents with High Selectivity against Colon Tumors

  摘要：

  A new class of potent and highly selective antitumor agents has been synthesized. Bisimidazoacridones, where the tetracyclic ring systems are held together by either a N-2-methyldiethylenetriamine or 3,3'-diamino-N-methyldipropylamine linker, and related asymmetrical compounds, where one of the imidazoacridone ring system was replaced by a triazoloacridone ring system, were found to be cytostatic and cytotoxic in vitro. Some of these compounds, such as 5,5'-[(methylimino)bis(3,1-propanediylimino)]bis[6H-imidazo[4,5,1-de]acridim-6-one] (4b) showed remarkably high activity and selectivity for colon cancer in the National Cancer Institute screen. This antitumor effect was also apparent in colony survival assays utilizing the colon cancer line, HCT-116, and in in vivo assays involving xenografts of tumor derived from HCT-116 in nude mice. The tested compounds exhibited relatively low acute toxicity and were well tolerated by the treated animals. The bisimidazoacridones interact with nucleic acids in vitro but preliminary experimental and modeling data indicate that in spite of their structure, they may not be bis-intercalators. While the precise mode of action of these compounds is not yet understood, they appear to be excellent candidates for clinical development.

  DOI：

  10.1021/jm00016a007
• 作为产物：
  描述：

  2,6-二氯-3-硝基苯甲酸 、 4-叔丁基苯胺 在 lithium carbonate 作用下， 以 丙醇 为溶剂， 反应 24.0h， 以65%的产率得到2-<(tert-butylphenyl)amino>-6-chloro-3-nitrobenzoic acid
  参考文献：
  名称：

  Bisimidazoacridones and Related Compounds: New Antineoplastic Agents with High Selectivity against Colon Tumors

  摘要：

  A new class of potent and highly selective antitumor agents has been synthesized. Bisimidazoacridones, where the tetracyclic ring systems are held together by either a N-2-methyldiethylenetriamine or 3,3'-diamino-N-methyldipropylamine linker, and related asymmetrical compounds, where one of the imidazoacridone ring system was replaced by a triazoloacridone ring system, were found to be cytostatic and cytotoxic in vitro. Some of these compounds, such as 5,5'-[(methylimino)bis(3,1-propanediylimino)]bis[6H-imidazo[4,5,1-de]acridim-6-one] (4b) showed remarkably high activity and selectivity for colon cancer in the National Cancer Institute screen. This antitumor effect was also apparent in colony survival assays utilizing the colon cancer line, HCT-116, and in in vivo assays involving xenografts of tumor derived from HCT-116 in nude mice. The tested compounds exhibited relatively low acute toxicity and were well tolerated by the treated animals. The bisimidazoacridones interact with nucleic acids in vitro but preliminary experimental and modeling data indicate that in spite of their structure, they may not be bis-intercalators. While the precise mode of action of these compounds is not yet understood, they appear to be excellent candidates for clinical development.

  DOI：

  10.1021/jm00016a007

文献信息

• Bis-acridone chemotherapeutic derivatives
  申请人：The United States America as represented by the Department of Health and

  公开号：US05508289A1

  公开（公告）日：1996-04-16

  The present invention provides an anticancer compound having the structure: ##STR1## wherein R is --H, --CH.sub.3, or --C.sub.2 H.sub.5 ; R1 and R2 are independently --H, --OH, --NH.sub.2, --OCH.sub.3, --C(CH.sub.3).sub.3, or a halogen atom; n is 2 to 6; X and X' are independently --N or --NO.sub.2 ; Y and Y' are independently --N, --CH, or --H; and the double-slash represents a double bond or no bond; such that when X or X' is --N, Y or Y' is --CH or --N, and the double-slash is a double bond, and when X or X' is --NO.sub.2, Y or Y' is --H, and the double-slash is no bond. The present invention also provides a pharmaceutical composition comprising the compound above and a pharmaceutically acceptable carrier.

  本发明提供了一种抗癌化合物，其结构为：##STR1## 其中R为--H，--CH.sub.3或--C.sub.2H.sub.5；R1和R2分别为--H，--OH，--NH.sub.2，--OCH.sub.3，--C(CH.sub.3).sub.3或卤素原子；n为2到6；X和X'分别为--N或--NO.sub.2；Y和Y'分别为--N，--CH或--H；双斜杠表示双键或无键；当X或X'为--N时，Y或Y'为--CH或--N，且双斜杠为双键，当X或X'为--NO.sub.2时，Y或Y'为--H，且双斜杠为无键。本发明还提供了一种包含上述化合物和药用载体的制药组合物。
• ACRIDONE-DERIVED BISINTERCALATORS AS CHEMOTHERAPEUTIC AGENTS
  申请人：THE UNITED STATES GOVERNMENT as represented by THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP0750612B1

  公开（公告）日：1999-12-15
• US5508289A
  申请人：——

  公开号：US5508289A

  公开（公告）日：1996-04-16
• [EN] ACRIDONE-DERIVED BISINTERCALATORS AS CHEMOTHERAPEUTIC AGENTS<br/>[FR] COMPOSES INTERCALAIRES BIFONCTIONNELS DERIVES D'ACRIDONE UTILISES EN TANT QU'AGENTS CHIMIOTHERAPEUTIQUES
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA, represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：WO1995025093A1

  公开（公告）日：1995-09-21

  (EN) The present invention provides a compound having structure (I), wherein R is -H, -CH3, or -C2H5; R1 and R2 are independently -H, -OH, -NH2, -OCH3, -C(CH3)3, or a halogen atom; n is 2 to 6; X and X' are independently -N or -NO2; Y and Y' are independently -N, -CH, or -H; and the double-slash represents a double bond or no bond; such that when X or X' is -N, Y or Y' is -CH or -N, and the double-slash is a double bond, and when X or X' is -NO2, Y or Y' is -H, and the double-slash is no bond. The present invention also provides a pharmaceutical composition comprising the compound above and a pharmaceutically acceptable carrier. The present invention further provides a method for treating a neoplastic cell growth in a subject in need of such treatment which comprises administering to the subject an amount of the pharmaceutical composition above effective to treat the neoplastic cell growth. Lastly, the present invention provides nucleic acid labeled with the compound above, as well as a method for detecting nucleic acid in a sample.(FR) L'invention concerne un composé possédant la structure (I) dans laquelle R représente -H, -CH3 ou -C2H5; R1 et R2 représentent indépendamment -H, -OH, -NH2, -OCH3, -C(CH3)3 ou un atome d'halogène; n représente 2 à 6; X et X' représentent indépendamment -N ou -NO2; Y et Y' représentent indépendamment -N, -CH ou -H et la double barre oblique représente une liaison double ou l'absence de liaison, de telle manière que, quand X ou X' représente -N, Y ou Y' représente -CH ou -N et la double barre oblique représente une liaison double, et quand X ou X' représente -NO2, Y ou Y' représente -H et la double barre oblique représente l'absence de liaison. L'invention concerne également une composition pharmaceutique comprenant ledit composé et un excipient pharmaceutiquement acceptable. Elle concerne encore un procédé de traitement d'une croissance cellulaire néoplasique chez un patient qui consiste à administrer une dose efficace de ladite composition audit patient, afin de traiter ladite croissance cellulaire. Elle concerne enfin un acide nucléique marqué au moyen dudit composé, ainsi qu'un procédé de détection d'acide nucléique dans un échantillon.
• Bisimidazoacridones and Related Compounds: New Antineoplastic Agents with High Selectivity against Colon Tumors
  作者：Wieslaw M. Cholody、Lidia Hernandez、Lawrence Hassner、Dominic A. Scudiero、Draginja B. Djurickovic、Christopher J. Michejda

  DOI：10.1021/jm00016a007

  日期：1995.8

  A new class of potent and highly selective antitumor agents has been synthesized. Bisimidazoacridones, where the tetracyclic ring systems are held together by either a N-2-methyldiethylenetriamine or 3,3'-diamino-N-methyldipropylamine linker, and related asymmetrical compounds, where one of the imidazoacridone ring system was replaced by a triazoloacridone ring system, were found to be cytostatic and cytotoxic in vitro. Some of these compounds, such as 5,5'-[(methylimino)bis(3,1-propanediylimino)]bis[6H-imidazo[4,5,1-de]acridim-6-one] (4b) showed remarkably high activity and selectivity for colon cancer in the National Cancer Institute screen. This antitumor effect was also apparent in colony survival assays utilizing the colon cancer line, HCT-116, and in in vivo assays involving xenografts of tumor derived from HCT-116 in nude mice. The tested compounds exhibited relatively low acute toxicity and were well tolerated by the treated animals. The bisimidazoacridones interact with nucleic acids in vitro but preliminary experimental and modeling data indicate that in spite of their structure, they may not be bis-intercalators. While the precise mode of action of these compounds is not yet understood, they appear to be excellent candidates for clinical development.