N1-ethyl-N2-phthalyl-1,2-ethanediamine | 697216-36-7

• 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: N1-ethyl-N2-phthalyl-1,2-ethanediamine
• 英文别名: N-[2-(ethylamino)ethyl]phthalimide；2-[2-(ethylamino)ethyl]isoindole-1,3-dione
• CAS: 697216-36-7
• 化学式: C₁₂H₁₄N₂O₂
• mdl: MFCD14648922
• 分子量: 218.255
• InChiKey: RSCNQDJBFZLIOM-UHFFFAOYSA-N

物化性质

• 熔点：
  232-235 °C(Solv: isopropanol (67-63-0))
• 沸点：
  349.5±25.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N1-ethyl-N2-phthalyl-1,2-ethanediamine 在 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 120.0h， 生成 N-[2-[N-ethyl-N-[2-(2-nitropyridin-3-yloxy)ethyl]amino]ethyl]phthalimide
  参考文献：
  名称：

  Single Photon Emission Computed Tomography/Positron Emission Tomography Imaging and Targeted Radionuclide Therapy of Melanoma: New Multimodal Fluorinated and Iodinated Radiotracers

  摘要：

  This study reports a series of 14 new iodinated and fluorinated compounds offering both early imaging (I-123, I-124, F-18) and systemic treatment (I-131) of melanoma potentialities. The biodistribution of each I-125-labeled tracer was evaluated in a model of melanoma B16F0 bearing mice, using in vivo serial gamma scintigraphic imaging. Among this series, [I-125]56 emerged as the most promising compound in terms of specific tumoral uptake and in vivo kinetic profile. To validate our multimodality concept, the radiosynthesis of [F-18]56 was then optimized and this radiotracer has been successfully investigated for in vivo PET imaging of melanoma in B16F0- and B16F10-bearing mouse model. The therapeutic efficacy of [I-131]56 was then evaluated in mice bearing subcutaneous B16F0 melanoma, and a significant slow down in tumoral growth was demonstrated. These data support further development of 56 for PET imaging (F-18, I-124) and targeted radionuclide therapy (I-131) of melanoma using a single chemical structure.

  DOI：

  10.1021/jm101574q
• 作为产物：
  描述：

  N-[2-(ethylamino)ethyl]-1H-phthalimide hydrochloride 在 disodium;carbonate 、 二氯甲烷 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 以to give compound 2 (1.41 g, 6.47 mmol) as a yellow solid的产率得到N1-ethyl-N2-phthalyl-1,2-ethanediamine
  参考文献：
  名称：

  Labelled analogues of halobenzamides as multimodal radiopharmaceuticals and their precursors

  摘要：

  本发明涉及公式（I）的化合物： 其中，R1代表氢原子，可选择标记的卤素，放射性核素或Sn[(C1-C4)烷基]3基团； Ar代表芳基或杂芳基； R9代表氢原子，(C1-C4)烷基或与基团R1-Ar一起形成与Ar基团融合的环； A代表公式（β）或（δ）的基团： R3和R4独立地代表氢原子，(C1-C6)烷基，(C1-C6)烯基或公式（γ）的基团： -Y-Z-W-R11（γ） 其中，R11代表可选择标记的卤素，放射性核素，芳基或杂芳基，可选择地被可选择标记的卤素，放射性核素，-NO2基团，-NR5R6基团，-N+R5R6R7X-基团或-OSO2R12基团取代； 以及与药学上可接受的酸形成的加成盐。 本发明还涉及包含它们的制药组合物以及它们在诊断中的应用，特别是在SPECT或PET成像中以及通过靶向放射性核素治疗黑色素瘤的治疗中的应用。

  公开号：

  US09125937B2

文献信息

• [EN] BENZAMIDE OR BENZAMINE COMPOUNDS USEFUL AS ANTICANCER AGENTS FOR THE TREATMENT OF HUMAN CANCERS<br/>[FR] COMPOSÉS BENZAMIDE OU BENZAMINE À UTILISER EN TANT QU'ANTICANCÉREUX POUR LE TRAITEMENT DE CANCERS HUMAINS
  申请人：UNIV TEXAS

  公开号：WO2017007634A1

  公开（公告）日：2017-01-12

  The described invention provides small molecule anti-cancer compounds for treating tumors that respond to cholesterol biosynthesis inhibition. The compounds selectively inhibit the cholesterol biosynthetic pathway in tumor-derived cancer cells, but do not affect normally dividing cells.

  所描述的发明提供了用于治疗对胆固醇生物合成抑制作出反应的肿瘤的小分子抗癌化合物。这些化合物选择性地抑制肿瘤来源的癌细胞中的胆固醇生物合成途径，但不影响正常分裂的细胞。
• Preparation of Mono<i>Boc</i>-Protected Unsymmetrical Diamines
  作者：Hongbo Li、Meng-an Hao、Liping Wang、Wu Liang、Kai Chen

  DOI：10.1080/00304940903077998

  日期：2009.7.22

  Monofunctionalized unsymmetrical diamines have been frequently used as starting materials in the synthesis of biological active agents and pharmacophores. 1 – 6 There have been some reports that ch...

  单官能化的不对称二胺经常被用作合成生物活性剂和药效团的原料。1 – 6 有一些报道称...
• LABELLED ANALOGUES OF HALOBENZAMIDES AS MULTIMODAL RADIOPHARMACEUTICALS AND THEIR PRECURSORS
  申请人：Chezal Jean-Michel

  公开号：US20110044899A1

  公开（公告）日：2011-02-24

  A compound of formula (I): in which R 1 represents a hydrogen atom, an optionally labelled halogen, a radionuclide or a Sn[(C 1 -C 4 )alkyl] 3 group, Ar represents an aryl group or a heteroaryl group, R 9 represents a hydrogen atom, a (C 1 -C 4 ) alkyl group or forms together with the group R 1 —Ar a ring fused with the Ar group, A represents a group of formula (β) or (δ): R 3 and R 4 independently represent a hydrogen atom, a (C 1 -C 6 )alkyl group, a (C 1 -C 6 ) alkenyl group or a group of formula (y): wherein R 11 represents an optionally labelled halogen, a radionuclide, an aryl or heteroaryl group optionally substituted by an optionally labelled halogen, a radionuclide, a —NO 2 group, a —NR 5 R 6 group, a N + R 5 R 6 R 7 X − group, or a —OSO 2 R 12 group, and their addition salts with pharmaceutically acceptable acids.

  化合物的化学式为(I)：其中R1代表氢原子、可选择标记的卤素、放射性核素或Sn[(C1-C4)烷基]3基团，Ar代表芳基或杂芳基，R9代表氢原子、(C1-C4)烷基或与基团R1-Ar共同形成与Ar基团融合的环，A代表化学式(β)或(δ)的基团：R3和R4分别独立地代表氢原子、(C1-C6)烷基、(C1-C6)烯基或化学式(y)的基团：其中R11代表可选择标记的卤素、放射性核素、可选择取代的芳基或杂芳基，取代基可以是可选择标记的卤素、放射性核素、—NO2基团、—NR5R6基团、N+R5R6R7X−基团或—OSO2R12基团，以及它们与药物可接受的酸形成的加合物。
• Labelled Quinoxaline Derivatives as Multimodal Radiopharmaceuticals and Their Precursors
  申请人：INSTITUT NATIONAL DE LA SANTET DE LA RECHERCHE MEDICALE

  公开号：US20150079000A1

  公开（公告）日：2015-03-19

  The present invention relates to the compound of formula (I), in which R1 represents Sn(R) 3 , B(OH) 2 , B(OR) 2 , a halogen atom, NO 2 , a radionuclide or a —N + (R) 3 group, where R is a (C 1 -C 6 ) alkyl group, R2 represents a hydrogen atom or a (C 1 -C 6 )alkyl group, R3 represents: a —(CH 2 CH 2 O) n2 —(CH 2 ) n3 —X group, or a —(CH 2 CH 2 O) n4 —(CH 2 ) n5 —Y group with Y representing a —C═C—H, a —N 3 or a —Ar—(CH 2 ) n6 —(OCH 2 CH 2 ) n7 —X group, and X represents a halogen atom, a radionuclide or a —OSO 2 R′ group, where R′ is a CF 3 , CH 3 , t-Bu, Ph, p-NO 2 Ph, p-BrPh or p-CH 3 Ph group, and their addition salts with pharmaceutically acceptable acids, The present invention also relates to pharmaceutical compositions comprising them and to their use in diagnosis, in particular with SPECT or PET imaging and in therapy of melanoma, via targeted radionuclide therapy.

  本发明涉及式（I）的化合物，其中R1代表Sn(R)3、B(OH)2、B(OR)2、卤素原子、NO2、放射性核素或—N+(R)3基团，其中R是(C1-C6)烷基，R2代表氢原子或(C1-C6)烷基，R3代表：—(CH2CH2O)n2—(CH2)n3—X基团，或—(CH2CH2O)n4—(CH2)n5—Y基团，其中Y代表—C═C—H、—N3或—Ar—(CH2)n6—(OCH2CH2)n7—X基团，X代表卤素原子、放射性核素或—OSO2R′基团，其中R′是CF3、CH3、t-Bu、Ph、p-NO2Ph、p-BrPh或p-CH3Ph基团，以及它们与药学上可接受的酸的加合盐。本发明还涉及包含它们的制药组合物以及它们在诊断中的使用，特别是在SPECT或PET成像和黑色素瘤的靶向放射性核素治疗中的使用。
• BENZAMIDE OR BENZAMINE COMPOUNDS USEFUL AS ANTICANCER AGENTS FOR THE TREATMENT OF HUMAN CANCERS
  申请人：THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM

  公开号：US20170114062A1

  公开（公告）日：2017-04-27

  The described invention provides small molecule anti-cancer compounds for treating tumors that respond to cholesterol biosynthesis inhibition. The compounds selectively inhibit the cholesterol biosynthetic pathway in tumor-derived cancer cells, but do not affect normally dividing cells.