2-((8-荧基甲基)氨基)-2-甲基-1,3-丙烷二醇 | 96403-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-((8-荧基甲基)氨基)-2-甲基-1,3-丙烷二醇
• 英文名称: 2-((8-Fluoranthenylmethyl)amino)-2-methyl-1,3-propanediol
• 英文别名: 1,3-Propanediol, 2-((8-fluoranthenylmethyl)amino)-2-methyl-；2-(fluoranthen-8-ylmethylamino)-2-methylpropane-1,3-diol
• CAS: 96403-45-1
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: BNZUDBQCSFCEQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2922199090

反应信息

• 作为产物：
  描述：

  8-fluoranthenecarbaldehyde 、 2-氨基-2-甲基-1,3-丙二醇 在 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 生成 2-((8-荧基甲基)氨基)-2-甲基-1,3-丙烷二醇
  参考文献：
  名称：

  2-[(Arylmethyl)amino]-2-methyl-1,3-propanediol DNA intercalators. An examination of the effects of aromatic ring variation on antitumor activity and DNA binding

  摘要：

  The effects of variation of aromatic ring size, shape, and side-chain position on antitumor activity and DNA binding in a series of carbocyclic 2-[(arylmethyl)amino]-2-methyl-1,3-propanediols (AMAPs) were examined. In general, the interaction of AMAPs with DNA increases as the intercalating ring system grows in area, with three distinct binding levels evident. Isomers from a specific ring system appear to bind DNA similarly. DNA binding is not the sole criterion for antitumor activity for the AMAPs studied; the magnitude of the DELTA-T(m) does not correlate with the antitumor activity observed. Significant in vivo P388 activity was seen for AMAP congeners from several tetracyclic ring systems. However, isomers from each of the specific ring systems produced a wide range of in vivo P388 activity. Thus, AMAP antitumor activity is not a function of the ring system per se, but rather appears to be related to the shape of the specific molecule. Three AMAP congeners (crisnatol (770U82, 773U82, and 502U83) are currently in clinical trials.

  DOI：

  10.1021/jm00111a010

文献信息

• Polycyclic aromatic compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0125701A2

  公开（公告）日：1984-11-21

  Compounds of the formula (I) or monomethyl or monoethyl ethers thereof, the compounds of formula (I) including their ethers containing no more than 30 carbon atoms in total, or esters or salts thereof; wherein Aris perylene,fluoranthene, chrysene, pyrene or triphenylene, optionally substituted by one or two substituents, or when Ar is anthracene or phenanthrene optionally substituted by one, two or three substituents; said substituents containing not more than four carbon atoms in total when taken together being the same or different and are selected from halogen; cyano; C1-4alkyl or C1-4alkoxy, each optionally substituted by hydroxy or C1-2alkoxy; halogen substituted Cl-2alkyl or C1-2alkoxy; halogen substituted Ci-2 alkyl or C1-2alkoxy; a group S(O)nR2 wherein n is an integer 0,1 or 2 and R2 is C1-2alkyl optionally substituted by hydroxy or C1- 2alkoxy; or Ar is optionally substituted by a group NR3R4 containing not more than 5 carbon atoms wherein R3 and R' are the same or different and each is a Ci-3alkyl group or NR3R4 forms a five-or six-membered heterocyclic ring optionally containing one or two additional heteroatoms; R' contains not more than eight carbon atoms and is a group or wherein m is 0 or 1; R5 is hydrogen or methyl; R6 and R' are the same or different and each is hydrogen or C1-3alkyl optionally substituted by hydroxy; R8 and R9 are the same or different and each is hydrogen or Ci-3alkyl; -C-C- is a five-or six-membered saturated carbocyclic ring; R10 is hydrogen, methyl or hydroxymethyl; R", R12 and R13 are the same or different and each is hydrogen or methyl; R14 is hydrogen, methyl, hydroxy, or hydroxymethyl; and provided that when Ar is 6-chrysenyl, 3- or 7-fluoranthenyl, 2-triphenylenyl, or 1- or 9-anthracenyl optionally substituted by one or two substituents as hereinbefore defined; other than optionally substituted butyl or butoxy R6 is C1-3alkyl optionally substituted by hydroxy; R7 is hydrogen, C1-3alkyl or hydroxymethyl; R'to R12 and R" are as hereinbefore defined; R13 is hydrogen; and m is 0; R5 is methyl, are disclosed as having biocidal and, in particular, antitumour activity. Methods for preparing the compounds, formulations containing them and their use in medicine are also described.

  式(I)化合物 或其单甲基醚或单乙基醚，式（I）化合物包括其总计含有不超过 30 个碳原子的醚，或其酯或盐；其中 Ar 为过ylene、fluoranthene、chrysene、pyrene 或 triphenylene，可任选被一个或两个取代基取代，或当 Ar 为 anthracene 或 phenanthrene 时，可任选被一个、两个或三个取代基取代；所述取代基在一起时总计含有不超过四个碳原子，可相同或不同，选自卤素、氰基、C1-4 烷基或 C1-4 烷氧基，各自可任选被羟基或 C1-2 烷氧基取代；卤素取代的 Cl-2 烷基或 C1-2 烷氧基；卤素取代的 C1-2 烷基或 C1-2 烷氧基；C1-4 烷基或 C1-4 烷氧基，各自可选被羟基或 C1-2 烷氧基取代；卤素取代的 Cl-2 烷基或 C1-2 烷氧基；卤素取代的 Ci-2 烷基或 C1-2 烷氧基；基团 S(O)nR2，其中 n 为整数 0、1 或 2，R2 为可选被羟基或 C1-2 烷氧基取代的 C1-2 烷基；或 Ar 被含有不超过 5 个碳原子的基团 NR3R4 任选取代，其中 R3 和 R'相同或不同，且各自为 Ci-3 烷基或 NR3R4 构成五或六元杂环，可任选含有一个或两个额外的杂原子；R'含有不超过 8 个碳原子，且是一个基团 或 其中 m 为 0 或 1； R5 是氢或甲基； R6 和 R' 相同或不同，各自为氢或任选被羟基取代的 C1-3 烷基； R8和R9相同或不同，各自为氢或Ci-3烷基； -C-C-是五或六元饱和碳环；R10 是氢、甲基或羟甲基；R"、R12 和 R13 相同或不同，且各自是氢或甲基；R14 是氢、甲基、羟基或羟甲基；且当 Ar 是 6-丙烯腈基、3-或 7-氟苯基、2-三苯烯基或 1-或 9-蒽基时，可任选被一个或两个如前定义的取代基取代；除任选取代的丁基或丁氧基外，R6 是任选被羟基取代的 C1-3 烷基；R7 是氢、C1-3 烷基或羟甲基；R'至 R12 和 R "如前定义；R13 是氢；m 是 0；R5 是甲基。此外，还描述了制备这些化合物的方法、含有这些化合物的制剂及其在医学中的用途。
• US4532344A
  申请人：——

  公开号：US4532344A

  公开（公告）日：1985-07-30
• US4720587A
  申请人：——

  公开号：US4720587A

  公开（公告）日：1988-01-19
• US4803222A
  申请人：——

  公开号：US4803222A

  公开（公告）日：1989-02-07
• US4808632A
  申请人：——

  公开号：US4808632A

  公开（公告）日：1989-02-28