ω-phthalimidododecanoyl chloride | 146918-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: ω-phthalimidododecanoyl chloride
• 英文别名: 12-(1,3-Dioxoisoindol-2-yl)dodecanoyl chloride
• CAS: 146918-05-0
• 化学式: C₂₀H₂₆ClNO₃
• 分子量: 363.884
• InChiKey: IVYPOJJIWCJIJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ω-phthalimidododecanoyl chloride 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 11.5h， 生成 N',N'-diethyl-N-(7-iodoquinolin-4-yl)dodecane-1,12-diamine
  参考文献：
  名称：

  Structure−Activity Relationships for Antiplasmodial Activity among 7-Substituted 4-Aminoquinolines

  摘要：

  Aminoquinolines (AQs) with diaminoalkane side chains (-HNRNEt2) shorter or longer than the isopentyl side chain [-HNCHMe(CH2)(3)NEt2] of chloroquine are active against both chloroquine-susceptible and -resistant Plasmodium falciparum. (De, D.; et al. Am. J. Trop. Med. Hyg. 1996, 55, 579-583). In the studies reported here, we examined structure-activity relationships (SARs) among AQs with different N,N-diethyldiaminoalkane side chains and different substituents at the 7-position occupied by Cl in chloroquine. 7-Iodo- and 7-bromo-AQs with diaminoalkane side chains [-HN(CH2)(2)NEt2, -HN(CH2)(3)NEt2, or -HNCHMeCH2NEt2] were as active as the corresponding 7-chloro-AQs against both chloroquine-susceptible and -resistant P. falciparum (IC(50)s of 3-12 nM). In contrast, with one exception, 7-fluoro-AQs and 7-trifluoromethyl-AQs were less active against chloroquine-susceptible P. falciparum (IC(50)s of 15-50 nM) and substantially less active against chloroquine-resistant P. falciparum (IC(50)s of 18-500 nM). Furthermore, most 7-OMe-AQs were inactive against both chloroquine-susceptible (IC(50)s of 17-150 nM) and -resistant P. falciparum (IC(50)s of 90-3000 nM).

  DOI：

  10.1021/jm980146x
• 作为产物：
  描述：

  苯酐 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 ω-phthalimidododecanoyl chloride
  参考文献：
  名称：

  组装中/长链基β -arylated非天然氨基酸通过加入Pd（II） -催化藻酸衍生物3 β -CH芳基化和短对咯利普兰型衍生物路线

  摘要：

  在本文中，我们报告了通过Pd（II）催化的双齿导向8-氨基喹啉辅助的β-芳基化短/中/长链基非α-氨基酸（氨基链酸）衍生物的文库的组装SP 3 β -CH激活/芳基化方法。在β-位包含芳基的基于短/中链的非天然氨基酸衍生物是具有治疗特性的有前途的小分子。因此，有必要丰富在β-位包含芳基的基于短/中/长链的非天然氨基酸衍生物的文库。考虑到基于β-芳基化的短链/中链/长链的非α的重要性α-氨基酸衍生物，包括性的关注了探索的Pd（II） -催化的SP 3 β -CH短/中的芳基化/长链为基础的非α -氨基酸。使用选择的β -CH芳基化的非α-氨基酸衍生物显示了代表性的合成转化，包括用于制备咯利普兰和相关化合物以及3-芳基化的GABA衍生物（如巴氯芬，苯丁酸和甲苯丁酸）的短路径。

  DOI：

  10.1016/j.tet.2019.03.018

文献信息

• Imidocarboxylic acid activators and sulfimidocarboxylic acid activators,
  申请人：Hoechst AG

  公开号：US05438147A1

  公开（公告）日：1995-08-01

  A persalt activator or salt thereof which is derived from an imidocarboyxlic acid or sulimidocarboxylic acid of the formula I: ##STR1## in which A is a group of the formula ##STR2## n is the number 0, 1 or 2, R.sup.1 is hydrogen, chlorine, bromine, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, aryl, or alkylaryl, R.sup.2 is hydrogen, chlorine, bromine or a group of the formula --SO.sub.3 M, --CO.sub.2 M or --OSO.sub.3 M, X is C.sub.1 -C.sub.19 -alkylene or arylene, B is a group of the formula C.dbd.O or SO.sub.2, and L is a leaving group.

  一种由公式I中的咪唑羧酸或亚咪唑羧酸衍生的过氧盐活化剂或其盐，其中公式I如下：##STR1## 其中A是以下公式的基团##STR2## n为数字0、1或2，R.sup.1为氢、氯、溴、C.sub.1 -C.sub.20 -烷基、C.sub.2 -C.sub.20 -烯基、芳基或烷基芳基，R.sup.2为氢、氯、溴或--SO.sub.3 M、--CO.sub.2 M或--OSO.sub.3 M的基团，X为C.sub.1 -C.sub.19 -烷基或芳基，B为C.dbd.O或SO.sub.2的基团，L为离去基团。
• Synthesis and antiherpetic activity of novel purine conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine
  作者：Olga А. Vozdvizhenskaya、Valeriya L. Andronova、Georgii А. Galegov、Galina L. Levit、Victor P. Krasnov、Valery N. Charushin

  DOI：10.1007/s10593-021-02929-z

  日期：2021.4

  A method for the synthesis of novel purine conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine containing fragments of ω-amino acids with different lengths of the polymethylene chain as a linker has been developed. It was found in experiments in vitro that the obtained compounds are active against the herpes simplex virus type 1, including the acyclovir-resistant strain.

  一种以7,8-二氟-3-甲基-3,4-二氢-2 H -1,4-苯并恶嗪为原料的新颖嘌呤偶联物的合成方法，所述ω-氨基酸片段具有不同的多亚甲基链长度。链接器已开发。在体外实验中发现，所获得的化合物对1型单纯疱疹病毒具有活性，包括抗阿昔洛韦的菌株。
• Biologically Compatible, Phosphorescent Dimetallic Rhenium Complexes Linked through Functionalized Alkyl Chains: Syntheses, Spectroscopic Properties, and Applications in Imaging Microscopy
  作者：Rebeca G. Balasingham、Flora L. Thorp-Greenwood、Catrin F. Williams、Michael P. Coogan、Simon J. A. Pope

  DOI：10.1021/ic201654d

  日期：2012.2.6

  A range of luminescent, dimetallic complexes based upon the rhenium fac-tricarbonyl diimine core, linked by aliphatic chains of varying lengths and functionality, have been synthesized and their photophysical properties examined. Each complex displays characteristic (MReLdiimineCT)-M-3 emission in aerated acetonitrile solution, with long lifetimes in the range of 129-248 ns and corresponding quantum yields in the range 3.2-8.0%. In aqueous solution, as opposed to acetonitrile, the complexes generally show a small hypsochromic shift in lambda(em) and an extension of the (MLCT)-M-3 lifetime, attributed to a hydrophobically driven association of the alkyl chains with the rhenium-bound diimine units. In live cell imaging experiments using MCF7 cells the complexes all show good uptake by non-energy dependent mechanisms without endosomal entrainment, and with varying propensity to localize in organelles. The degrees of uptake and localization properties are discussed in terms of the length and chemical nature of the linkers, and in terms of the likely interactions between these and the various cellular components encountered.
• ——
  作者：Dibyendu De、Donald, J. Krogstad、Joel T. Mague

  DOI：10.1023/a:1022810821793

  日期：——

  The preparation of N-12-(7-chloro-4-quinolinyl)-N-1,N-1-diethyl-1,12-diaminododecane, AQ-40, was accomplished by a five-step process in 80% overall yield from 12-aminododecanoic acid and 4,7-dichloroquinoline. AQ-40 crystallizes as a monohydrate from reagent grade chloroform/ diethyl ether mixtures in the triclinc space group P-1 with a = 8.667(2), b = 8.9425(10), c = 17.217(3) Angstrom, alpha = 99.34(1), beta = 99.89(2), gamma = 91.56(1)degrees V = 1295.0 Angstrom(3) and Z = 2. The 12-(N-1,N-1-diethylamino)dodecyl side chain is in the fully extended conformation and the water molecule forms hydrogen bonds to the two tertiary nitrogen atoms as well as with the secondary amino group. The nitrogen of the secondary amino group bound to the four-position of the quinoline moiety is virtually planar. This together with the rather short C-N distance of 1.347(3) Angstrom to the quinoline moiety suggests involvement of the lone pair on this nitrogen with the pi system of the ring.
• US5438147A
  申请人：——

  公开号：US5438147A

  公开（公告）日：1995-08-01