N,N'-bis[4-(dimethylaminophenyl)methyl]butane-1,4-diamine | 363179-09-3

• 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: N,N'-bis[4-(dimethylaminophenyl)methyl]butane-1,4-diamine
• 英文别名: N,N'-bis[4-(dimethylamino)benzyl]-1,4-butanediamine；N,N'-bis[(4-dimethylaminophenyl)methyl]butane-1,4-diamine；N,N'-bis[[4-(dimethylamino)phenyl]methyl]butane-1,4-diamine
• CAS: 363179-09-3
• 化学式: C₂₂H₃₄N₄
• 分子量: 354.539
• InChiKey: VHJGPBPUDZKERJ-UHFFFAOYSA-N

物化性质

• 熔点：
  59-60 °C
• 沸点：
  508.6±45.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  30.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cucurbituril 、 N,N'-bis[4-(dimethylaminophenyl)methyl]butane-1,4-diamine 以 水 为溶剂， 生成
  参考文献：
  名称：

  N，N'-双[4-（二甲基氨基苯基）甲基]丁烷-1,4-二胺与葫芦巴[ n ]基团 之间的主客体相互作用研究（n = 6，7）†

  摘要：

  n = 6或7的cuucuribit [ n ] urils （Q [ n ]）与客体N，N'-双[4-（二甲基氨基苯基）甲基]丁烷-1,4-二胺（G）之间的相互作用已通过1 H NMR光谱，电子吸收光谱和等温滴定量热法（ITC）在水溶液中进行了研究。在Q [6]的情况下，倾向于使用1：1的主宾复合体，G的一端最初嵌入Q [6]中，尽管随着时间的推移（48小时），Q [6]沿着链穿梭这样它就位于G的中心上。对于Q [7]，形成一个2：1的主体-客体复合物，在G的每个末端都带有芳香基埋在Q [7]腔中。确定了整体组成为Q [6]· G H 2 ·2Cl·14H 2 O的包合物的分子结构，清楚地显示了客体分子与宿主Q [6]的插入并被定位其中有两个N–H⋯O氢键。

  DOI：

  10.1039/c9nj03254a
• 作为产物：
  描述：

  N,N'-bis(dimethylamionobenzylidene)butane-1,4-diamine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到N,N'-bis[4-(dimethylaminophenyl)methyl]butane-1,4-diamine
  参考文献：
  名称：

  Synthesis and evaluation of hexahydropyrimidines and diamines as novel hepatitis C virus inhibitors

  摘要：

  In order to identify novel anti-hepatitis C virus (HCV) agents we devised cell-based strategies and screened phenotypically small molecule chemical libraries with infectious HCV particles, and identified a hit compound (1) containing a hexahydropyrimidine (HHP) core. During our cell-based SAR study, we observed a conversion of HHP 1 into a linear diamine (6), which is the active component in inhibiting HCV and exhibited comparable antiviral activity to the cyclic HHP I. In addition, we engaged into the biological characterization of HHP and demonstrated that HHP does not interfere with HCV RNA replication, but with entry and release of viral particles. Here we report the results of the preliminary SAR and mechanism of action studies with HHP. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.055

文献信息

• [EN] COMPOSITIONS AND METHODS FOR TREATING DISEASES AND CONDITIONS<br/>[FR] COMPOSITIONS ET MÉTHODES POUR LE TRAITEMENT DE MALADIES ET D'ÉTATS PATHOLOGIQUES
  申请人：UNIV PITTSBURGH

  公开号：WO2016094659A1

  公开（公告）日：2016-06-16

  A compound of Formula II, or a salt, ester, solvate, hydrate or prodrug thereof: where: X1 is a branched or unbranched C1-10 alkyl, (CH2)s-NH-(CH2)t, (CH2)s-0-(CH2)t, or (CH2)S-C(NH2)- (CH2)v-NH-(CH2)t,where s, t and v are each, independently an integer from 1 to 5; A and B are each, independently, C6-10 aryl, C6-10aryl-C1-6alkyl, C3-9 heteroaryl, or C3-9heteroaryl-C1- 6alkyl, each optionally substituted with 1, 2 or 3 independently selected Rg groups; C and D are each, independently, C3-7 cycloalkyl, C3-7 cycloalkyl-C1-6alkyl, C3-7 heterocycloalkyl, C3-7 heterocycloalkyl-C1-6 alkyl, C6-10aryl, C6-10aryl-C1-6alkyl, C3-9 heteroaryl, or C3-9heteroaryl-C1-6alkyl, each optionally substituted with 1, 2 or 3 independently selected Rg groups; each Rg is, independently, halogen, C1-6 alkyl, C1-6 haloalkyl, hydroxyl, C1-6 alkoxy, C1-6 haloalkoxy, amino, C1-6alkylamino, or di-C1-6alkylamino; and n1 and p1 are each, independently, integers from 1 to 10.

  Formula II的化合物，或其盐、酯、溶剂合物、水合物或前药：其中：X1是支链或非支链的C1-10烷基，(CH2)s-NH-(CH2)t，(CH2)s-0-(CH2)t，或(CH2)S-C(NH2)-(CH2)v-NH-(CH2)t，其中s、t和v分别是1到5之间的整数；A和B分别是独立的C6-10芳基、C6-10芳基-C1-6烷基、C3-9杂芳基或C3-9杂芳基-C1-6烷基，每个都可以选择性地用1、2或3个独立选择的Rg基团取代；C和D分别是独立的C3-7环烷基、C3-7环烷基-C1-6烷基、C3-7杂环烷基、C3-7杂环烷基-C1-6烷基、C6-10芳基、C6-10芳基-C1-6烷基、C3-9杂芳基或C3-9杂芳基-C1-6烷基，每个都可以选择性地用1、2或3个独立选择的Rg基团取代；每个Rg是独立的卤素、C1-6烷基、C1-6卤代烷基、羟基、C1-6烷氧基、C1-6卤代烷氧基、氨基、C1-6烷基氨基或二C1-6烷基氨基；n1和p1分别是独立的1到10之间的整数。
• Palladium-Catalyzed Suzuki-Miyaura Reaction of Aryl Chlorides in Aqueous Media Using Tetrahydrodiazepinium Salts as Carbene Ligands
  作者：Ismail Özdemir、Nevin Gürbüz、Yetkin Gök、Engin Çetinkaya、Bekir Çetinkaya

  DOI：10.1055/s-2005-872673

  日期：——

  A highly effective, easy to handle, and environmentally benign process for palladium-mediated Suzuki cross-coupling was developed. The in situ prepared three-component system of Pd(OAc)2, 1,3-dialkyltetrahydrodiazepinium chlorides (2a-e), and K2CO3 catalyzes quantitatively the Suzuki-Miyaura cross-coupling of deactivated aryl chloride.

  开发了一种高效、易于操作且对环境无害的钯介导Suzuki交叉偶联反应工艺。原位制备的三组分体系Pd(OAc)2、1,3-二烷基四氢二氮杂萘氯盐（2a-e）和K2CO3能够定量催化不活泼芳香氯的Suzuki-Miyaura交叉偶联反应。
• Compositions and methods for treating diseases and conditions
  申请人：University of Pittsburgh—Of the Commonwealth System of Higher Education

  公开号：US10487076B2

  公开（公告）日：2019-11-26

  A compound of Formula II, or a salt, ester, solvate, hydrate or prodrug thereof: where: X1 is a branched or unbranched C1-10 alkyl, (CH2)s—NH—(CH2)t, (CH2)s—O—(CH2)t, or (CH2)s—C(NH2)—(CH2)v—NH—(CH2)t, where s, t and v are each, independently an integer from 1 to 5; A and B are each, independently, C6-10aryl, C6-10aryl-C1-6alkyl, C3-9 heteroaryl, or C3-9heteroaryl-C1-6alkyl, each optionally substituted with 1, 2 or 3 independently selected Rg groups; C and D are each, independently, C3-7 cycloalkyl, C3-7 cycloalkyl-C1-6alkyl, C3-7 heterocycloalkyl, C3-7 heterocycloalkyl-C1-6 alkyl, C6-10aryl, C6-10aryl-C1-6alkyl, C3-9 heteroaryl, or C3-9heteroaryl-C1-6alkyl, each optionally substituted with 1, 2 or 3 independently selected Rg groups; each Rg is, independently, halogen, C1-6 alkyl, C1-6 haloalkyl, hydroxyl, C1-6 alkoxy, C1-6 haloalkoxy, amino, C1-6 alkylamino, or di-C1-6alkylamino; and n1 and p1 are each, independently, integers from 1 to 10.

  式 II 的化合物或其盐、酯、溶液、水合物或原药： 其中 X1 是支链或未支链的 C1-10 烷基、(CH2)s-NH-(CH2)t、(CH2)s-O-(CH2)t 或 (CH2)s-C(NH2)-(CH2)v-NH-(CH2)t ，其中 s、t 和 v 各自独立地为 1 至 5 的整数； A 和 B 各自独立为 C6-10 芳基、C6-10 芳基-C1-6烷基、C3-9 杂芳基或 C3-9 杂芳基-C1-6烷基，各自任选被 1、2 或 3 个独立选择的 Rg 基团取代； C 和 D 各自独立为 C3-7 环烷基、C3-7 环烷基-C1-6烷基、C3-7 杂环烷基、C3-7 杂环烷基-C1-6烷基、C6-10 芳基、C6-10 芳基-C1-6烷基、C3-9 杂芳基或 C3-9 异芳基-C1-6烷基，各自任选被 1、2 或 3 个独立选择的 Rg 基团取代； 每个 Rg 独立地是卤素、C1-6 烷基、C1-6 卤代烷基、羟基、C1-6 烷氧基、C1-6 卤代烷氧基、氨基、C1-6 烷基氨基或二-C1-6 烷基氨基；以及 n1 和 p1 各自独立地为 1 至 10 的整数。
• Induction of apoptosis by aryl-substituted diamines: role of aromatic group substituents and distance between nitrogens
  作者：Mark R Burns、Solveig LaTurner、Josh Ziemer、Maralee McVean、Bruce Devens、C.Lance Carlson、Gerard F Graminski、Scott M Vanderwerf、Reitha S Weeks、Jay Carreon

  DOI：10.1016/s0960-894x(02)00156-7

  日期：2002.5

  A series of aromatic substituted diamines was synthesized and characterized for their cytotoxic profiles against human breast and prostate tumor cell lines. Following a structure function analysis of the effects of changes of the benzyl substituents and the distance between amino groups the most potent analogues were analyzed biologically and were shown to induce apoptosis. These compounds do not induce the enzyme SSAT or deplete intracellular polyamine levels, mechanisms demonstrated by other cytotoxic polyamine analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.
• COMPOSITIONS AND METHODS FOR TREATING DISEASES AND CONDITIONS
  申请人：University of Pittsburgh - Of the Commonwealth System of Higher Education

  公开号：EP3230254B1

  公开（公告）日：2021-09-22