(5H-dibenzocyclohepten-5-yl)methylamine | 13055-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: (5H-dibenzocyclohepten-5-yl)methylamine
• 英文别名: 5-aminomethyl-5H-dibenzo[a,d]heptene；5-Aminomethyl-5H-dibenzocyclohepten；5H-Dibenzocyclohepten-5-methylamin；5-aminomethyl-5H-dibenzo[a,d]cycloheptene；C-(5H-Dibenzo[a,d]cyclohepten-5-yl)-methylamine；2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenylmethanamine
• CAS: 13055-68-0
• 化学式: C₁₆H₁₅N
• 分子量: 221.302
• InChiKey: BKZVRYQHIBSITO-UHFFFAOYSA-N

物化性质

• 熔点：
  97.5-98.3 °C
• 沸点：
  387.0±11.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5H-dibenzocyclohepten-5-yl)methylamine 、 乙酸酐 以100%的产率得到
  参考文献：
  名称：

  KIMOTO SHOSHICHIRO; IWAMOTO NORIKO; FUJIWARA YASUHIRO; OKAMOTO MASAO; ODA+, YAKUGAKU DZASSI, YAKUGAKU ZASSNI, J. PHARM. SOS. JAR., 1980, 100, NO 11, +

  摘要：

  DOI：
• 作为产物：
  描述：

  5H-二苯并[A,D]环庚烯,5-氯- 在 氨 、 氢气 、 镍 作用下， 以 乙醇 、 乙腈 为溶剂， 60.0~80.0 ℃ 、6.08 MPa 条件下， 反应 6.5h， 生成 (5H-dibenzocyclohepten-5-yl)methylamine
  参考文献：
  名称：

  New triazine derivatives as potent modulators of multidrug resistance

  摘要：

  A series of 70 triazine derivatives have been synthesized and tested for their capacity to modulate multidrug resistance (MDR) in DC-3F/AD and KB-A1 tumor cells in vitro, in comparison with verapamil (VRP), a calcium channel antagonist currently used in therapy as an antihypertensive drug, which also shows MDR modulating activity. Among the 12 selected compounds, 16 (S9788) showed high MDR reversing properties in vitro (300- and 6-fold VRP at 5-mu-M in DC-3F/AD and KB-A1 cells, respectively) and induced a strong accumulation of adriamycin. The relationship between the increase of ADR accumulation and the fold reversal induced by these compounds and their lack of effects on the sensitive DC-3F cells suggest that they act mainly by inhibiting the P-glycoprotein (Pgp) catalyzed efflux of cytotoxic agents, as already described for a majority of MDR modulators. In vivo, in association with the antitumor drug vincristine (0.25 mg/kg), 16 (100 mg/kg) increased the TIC by 39% in mice bearing the resistant tumor cell line P388/VCR. According to these interesting properties, 16 was selected for a clinical development because it was more bioavailable than 34, even though it was less active.

  DOI：

  10.1021/jm00091a017

文献信息

• 5-Formamidomethyl-5H-dibenzo[a,d]cycloheptene derivatives
  申请人：Merck & Co., Inc.

  公开号：US03992445A1

  公开（公告）日：1976-11-16

  This invention relates to derivatives of dibenzocycloheptenes. In particular, the invention relates to dibenzocycloheptenes which are substituted at the 5-position with an aminomethyl group and to methods of preparing the same. The invention also relates to intermediates which are useful in the preparation of the above compounds and to methods for preparing the same.

  本发明涉及二苯环庚烯的衍生物。具体而言，本发明涉及在5位取代有氨甲基基团的二苯环庚烯以及其制备方法。本发明还涉及在上述化合物的制备中有用的中间体以及其制备方法。
• New Purines and Purine Analogs as Modulators of Multidrug Resistance
  作者：Alain Dhainaut、Gilbert Regnier、Andre Tizot、Alain Pierre、Stephane Leonce、Nicolas Guilbaud、Laurence Kraus-Berthier、Ghanem Atassi

  DOI：10.1021/jm960361i

  日期：1996.1.1

  A series of 36 purine and purine analog derivatives have been synthesized and tested for their ability to modulate multidrug resistance in vitro (P388/VCR-20 and KB-A1 cells) and in vivo (P388/VCR leukemia). Compounds were compared to S9788, a triazine derivative which has already shown some activity during phase 1 clinical trials and also a limiting cardiovascular side effect possibly linked to its calcium channel affinity. The fact that active compounds increase adriamycin accumulation in the resistant KB-A1 cells, and not in the sensitive KB-3-1 cells, suggests they act predominantly by inhibiting the P-glycoprotein-catalyzed efflux of cytotoxic agents. No direct relation was found between the affinity for the phenylalkylamine binding site of the calcium channel and in vitro sensitization of resistant cells. In vivo, when administered po in association with vincristine (0.25 mg/kg), five compounds (3, 4, 9, 25, and 26), of very differing calcium channel affinities (K-i from 5 to 560 nM), fully restored (T/V greater than or equal to 1.4) the sensitivity of P388/VCR leukemia to vincristine.
• Teodori, Elisabetta; Dei, Silvia; Garnier-Suillerot, Arlette, Medicinal Chemistry Research, 2001, vol. 10, # 9, p. 563 - 576
  作者：Teodori, Elisabetta、Dei, Silvia、Garnier-Suillerot, Arlette、Quidu, Patricia、Scapecchi, Serena、Budriesi, Roberta

  DOI：——

  日期：——
• JPS5655390A
  申请人：——

  公开号：JPS5655390A

  公开（公告）日：1981-05-15
• US3992445A
  申请人：——

  公开号：US3992445A

  公开（公告）日：1976-11-16