2,6-二甲基二苯并[b,d]噻吩 | 97141-40-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2,6-二甲基二苯并[b,d]噻吩
• 英文名称: 1,8-di(ethylamino)-4-azaoctane
• 英文别名: 1,8-bis(ethyl)spermidine；1,4-Butanediamine, N-ethyl-N'-(3-(ethylamino)propyl)-；N-ethyl-N'-[3-(ethylamino)propyl]butane-1,4-diamine
• CAS: 97141-40-7
• 化学式: C₁₁H₂₇N₃
• 分子量: 201.355
• InChiKey: OPGANUOFXWVURM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N¹,N⁴,N⁸-tris(mesitylenesulfonyl)spermidine 在 氢溴酸 、 sodium hydride 、 苯酚 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 36.5h， 生成 2,6-二甲基二苯并[b,d]噻吩
  参考文献：
  名称：

  A Comparison of Structure−Activity Relationships between Spermidine and Spermine Analogue Antineoplastics

  摘要：

  A systematic investigation of the impact of spermidine analogues both in vitro and in vivo is described. The study characterizes the effects of these analogues on L1210 cell growth, polyamine pools, ornithine decarboxylase, S-adenosyl-L-methionine decarboxylase, spermidine/spermine N-1-acetyltransferase, the maintenance of cellular charge, i.e., cationic equivalence associated with the polyamines and their analogues, and compares their ability to compete with spermidine for transport. The findings clearly demonstrate that the activity of-the linear polyamine analogues is highly dependent on the length of the triamines and the size of the N-alpha,N-omega-substituents. It appears that there is an optimum chain length for various activities and that the larger the N-alpha,N-omega-alkyls, the less active the compound. Metabolic transformation including N-dealkylation of these compounds is also evaluated. While there is no monotonic relationship between chain length and the ability of the analogue to be metabolized, the dipropyl triamines are clearly more actively catabolized than the corresponding methyl and ethyl systems. A comparison of the triamines with the corresponding tetraamines is made throughout the text regarding both in vitro activity against L1210 cells and in vivo toxicity measurements, suggesting that several triamine analogues may offer therapeutic advantages over the corresponding tetraamines.

  DOI：

  10.1021/jm960849j

文献信息

• Analogs of biologically active, naturally occurring polyamines, pharmaceutical compositions and methods of treatment
  申请人：——

  公开号：US20030100615A1

  公开（公告）日：2003-05-29

  Polyamines having the formula: 1 or a salt thereof with a pharmaceutically acceptable acid wherein: R 1 -R 6 may be the same or different and are alkyl, aryl, aryl alkyl, cycloalkyl, optionally having an alkyl chain interrupted by at least one etheric oxygen atom, or hydrogen; N 1 , N 2 , N 3 and N 4 are nitrogen atoms capable of protonation at physiological pH's; a and b may be the same or different and are integers from 1 to 4; A, B and C may be the same or different and are bridging groups which effectively maintain the distance between the nitrogen atoms such that the polyamines: (i) are capable of uptake by a target cell upon administration thereof to a human or non-human animal; and (ii) upon uptake by the target cell, competitively bind via an electrostatic interaction between the positively charged nitrogen atoms to substantially the same biological counter-anions as the intracellular natural polyamines in the target cell; the polyamines, upon binding to the biological counter-anion in the cell, function in a manner biologically different than the intracellular polyamines, the polyamines not occurring in nature; as well as pharmaceutical compositions embodying the polyamines and methods of treating patients requiring anti-neoplastic therapy.

  聚胺具有以下化学式：1或其与药用可接受酸盐，其中：R1-R6可能相同或不同，为烷基、芳基、芳基烷基、环烷基，或可由至少一个醚氧原子中断的烷基链组成，或氢；N1、N2、N3和N4是氮原子，在生理pH下能够质子化；a和b可能相同或不同，为1至4的整数；A、B和C可能相同或不同，是有效维持氮原子之间距离的桥联基团，使得聚胺：(i)能够在给予人类或非人类动物后被靶细胞吸收；以及(ii)在被靶细胞吸收后，通过正电荷氮原子之间的静电相互作用与靶细胞内的天然聚胺基本相同地与生物学反离子结合；这些聚胺在细胞内与生物反离子结合后，以生物学上与细胞内聚胺不同的方式发挥作用，这些聚胺在自然界中不存在；以及包含聚胺的药物组合物和治疗需要抗肿瘤治疗的患者的方法。
• [EN] POLYAMINE PRODRUGS AND POLYAMINE PRODRUG FORMULATIONS<br/>[FR] PROMÉDICAMENTS DE POLYAMINE ET FORMULATIONS DE PROMÉDICAMENT DE POLYAMINE
  申请人：UNIV NEBRASKA

  公开号：WO2019173446A1

  公开（公告）日：2019-09-12

  Provided herein are copolymers comprising monomers of a polyamine and a degradable linker, and further comprising a stabilizing moiety, a fluorinated moiety, a poly(ethylene glycol) (PEG) which is optionally substituted with a targeting moiety, or a combination thereof. Also provided are nanoparticles comprising copolymers as described herein, and methods of using the copolymers and nanoparticles for treating diseases or disorders, e.g., Snyder Robinson Disease or cancer.

  本文提供了由聚胺和可降解连接剂单体组成的共聚物，进一步包括稳定基团、氟化基团、聚乙二醇（PEG），可选择用靶向基团替代，或其组合。本文还提供了包括上述共聚物的纳米粒子，并提供了使用这些共聚物和纳米粒子治疗疾病或疾病的方法，例如Snyder Robinson病或癌症。
• AMINOQUINOLINE DERIVATIVES AND USES THEREOF
  申请人：THE MCLEAN HOSPITAL CORPORATION

  公开号：US20150023930A1

  公开（公告）日：2015-01-22

  Described herein are aminoquinoline and aminoacridine based hybrids, pharmaceutical compositions and medicaments that include such aminoquinoline and aminoacridine based hybrids, and methods of using such compounds for diagnosing and/or treating infections, neurodegerative diseases or disorders, inflammation, inflammation associated diseases and disorders, and/or diseases or disorders that are treatable with dopamine agonists such as the restless leg syndrome.

  本文描述了基于氨基喹啉和氨基蒽醌的混合物，包括含有这种基于氨基喹啉和氨基蒽醌的混合物的制药组合物和药物，以及使用这种化合物诊断和/或治疗感染、神经退行性疾病或障碍、炎症、与炎症相关的疾病和障碍以及可用多巴胺激动剂治疗的疾病或障碍（如不宁腿综合征）的方法。
• Biologically active spermidine analogues, pharmaceutical compositions and methods of treatment
  申请人：——

  公开号：US20020045780A1

  公开（公告）日：2002-04-18

  Polyamines having the formula: 1 or a salt thereof with a pharmaceutically acceptable acid wherein: R 1 -R 5 may be the same or different and are alkyl, aryl, aryl alkyl, cycloalkyl or hydrogen; at least one of R 1 and R 2 and at least one of R 4 and R 5 are not hydrogen, and any of the alkyl chains may optionally be interrupted by at least one etheric oxygen atom, excluding N 1 ,N 3 -diethylspermidine and N 1 ,N 3 -dipropylspermidine; and A and B are bridging groups which effectively maintain the distance between the nitrogen atoms such that the polyamine: (i) is capable of uptake by a target cell upon administration of the polyamine to a human or non-human animal; and (ii) upon uptake by the target cell, competitively binds via an electrostatic interaction between the positively charged nitrogen atoms to substantially the same biological counter-anions as the intracellular natural polyamines in the target cell.

  具有以下公式1或其药学上可接受的酸盐的多胺，其中：R1-R5可以相同或不同，且为烷基，芳基，芳基烷基，环烷基或氢；R1和R2中至少有一个，以及R4和R5中至少有一个不是氢，任何烷基链都可以选择性地被至少一个醚氧原子中断，但不包括N1，N3-二乙基亚精胺和N1，N3-二丙基亚精胺；A和B是桥接基团，有效地保持氮原子之间的距离，使得多胺：（i）在将多胺用于人类或非人类动物的治疗时，能够被目标细胞吸收；（ii）在被目标细胞吸收后，通过正电荷氮原子之间的静电相互作用与目标细胞中的细胞内天然多胺基本相同地竞争性结合生物计数离子。
• Novel polyamine analog conjugates and quinone conjugates as therapies for cancers and prostate diseases
  申请人：SLIL Biomedical Corporation

  公开号：US20040006049A1

  公开（公告）日：2004-01-08

  Peptide conjugates in which cytocidal and cytostatic agents, such as polyamine analogs or naphthoquinones, are conjugated to a polypeptide recognized and cleaved by enzymes such as prostate-specific antigen (PSA) and cathepsin B are provided, as well as compositions comprising these conjugates. Methods of using these conjugates in the treatment of prostate diseases are also provided.

  本发明提供了肽共轭物，其中将细胞毒性和细胞增殖抑制剂，如多胺类似物或萘醌类化合物，与被酶如前列腺特异性抗原（PSA）和半胱氨酸蛋白酶B识别和切割的多肽共轭。同时提供了包含这些共轭物的组合物。本发明还提供了使用这些共轭物治疗前列腺疾病的方法。