N-(2''-mercaptoethyl)-2-((2'-mercaptoethyl)amino)acetamide | 202582-38-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2''-mercaptoethyl)-2-((2'-mercaptoethyl)amino)acetamide
• 英文别名: N-(2-Mercaptoethyl)-2-((2-mercaptoethyl)amino)acetamide；N-(2-sulfanylethyl)-2-(2-sulfanylethylamino)acetamide
• CAS: 202582-38-5
• 化学式: C₆H₁₄N₂OS₂
• 分子量: 194.322
• InChiKey: DUFJOYNZMOTOBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  potassium hydroxide 、 nickel(II) acetate tetrahydrate 、 N-(2''-mercaptoethyl)-2-((2'-mercaptoethyl)amino)acetamide 以 甲醇 为溶剂， 以75.9%的产率得到K(Ni(N-(2''-mercaptoethyl)-2-((2'-mercaptoethyl)amino)acetamide(-3H)))
  参考文献：
  名称：

  双酰胺和混合胺/酰胺 NiN2S2 配合物作为含镍乙酰辅酶 A 合酶和超氧化物歧化酶的模型：实验和计算研究

  摘要：

  乙酰辅酶A合酶（Ni d -ACS）和还原镍超氧化物歧化酶（Ni-SOD）的远端镍位点显示出类似的方形平面Ni II N 2 S 2配位环境。然而，这两个位点之间的一个区别是 Ni-SOD 中的镍离子包含混合的胺/酰胺配位基序，而Ni-ACS 中的 Ni d位点包含双酰胺基配位基序。为了深入了解不同配位环境对 Ni 离子性质的影响，我们系统地检查了两种方形平面 Ni II N 2 S 2复合物，一种具有双硫醇-双酰胺连接 (Et 4 N)2 (Ni(L1))·2H 2 O ( 2 ) [H 4 L1 = N -(2-巯基乙酰基)- N '-(2-巯基乙基)甘氨酰胺] 和另一个与双硫醇胺/酰胺基连接 K(Ni( HL2)) ( 3 ) [H 4 L2 = N -(2''-巯基乙基)-2-((2'-巯基乙基)氨基)乙酰胺]。尽管这两种配合物的区别仅在于单个胺与酰胺配体，但它们的化学性质却大不相同。双酰胺配合物

  DOI：

  10.1021/ic9023053
• 作为产物：
  描述：

  N-[2-[(triphenylmethyl)thio]ethyl]-2-[[2-[(triphenylmethyl)thio]ethyl]amino]acetamide 在 三乙基硅烷 、 三氟乙酸 、 2-巯基乙醇 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(2''-mercaptoethyl)-2-((2'-mercaptoethyl)amino)acetamide
  参考文献：
  名称：

  Preparation of99mTc-N2S2 conjugates of chrysamine G, potential probes for the beta-amyloid protein of Alzheimer's disease

  摘要：

  Chrysamine G is known to bind in vitro to the beta-amyloid protein (A beta 10-43) and to homogenates of several regions of brain of Alzheimer's patients. The purpose of this study was to develop a Tc-99m-labelled derivative of chrysamine G, in which the structural requirements for beta-amyloid affinity are preserved,Bis-S-trityl protected monoamide-monoaminedithiol (MAMA-Tr-2), a chelating system used to incorporate Tc-99m, was coupled with 2-(chloroacetylamino)-chrysamine G diethyl ester (4) yielding 2-(MAMA-Tr-2-acetylamino)-chrysamine G diethyl ester (5-Tr-2) To prepare 4, 4,4'-dinitro-2-biphenylamine was treated with chloroacetyl chloride to obtain 2-(chloroacetylamino)-4,4'-dinitrobiphenyl, of which the nitro functions were reduced by catalytic hydrogenation. Diazotation of 2-(chloroacetylamino)-4,4'-diaminobiphenyl, followed by coupling with ethyl salicylate provided 4 in an overall yield of 4.3 %. Alkaline hydrolysis of 5-Tr2 resulted in the monoethyl ester derivative (6-Tr-2) and diacid derivative (7-Tr-2) Detritylation acid labelling with Tc-99m was performed in the presence of Sn2+ and (TcO4-)-Tc-99m solution at pH 2-3 with heating. RP-HPLC analysis showed one peak for both the diester derivative (Tc-99m-5) and the diacid derivative (Tc-99m-7), while two peaks (A and B) were present for the monoethyl ester derivative (Tc-99m-6), probably isomers with respect to the ester position. The order of elution from RP-HPLC reflected the lipophilicity of the Tc-99m-complexes as determined by partitioning between l-octanol and phosphate buffer pH 7.4 (log P: Tc-99m-5 = 2.15, Tc-99m-6(A) = 1.79, Tc-99m-6(B) = 1.93, Tc-99m-7 = 1.08).

  DOI：

  10.1002/(sici)1099-1344(199904)42:4<309::aid-jlcr192>3.0.co;2-o

文献信息

• BIFUNCTIONAL COMPOUND WITH MONOSACCHARIDE AND N2S2 LIGAND, AND PREPARATION AND USE THEREOF
  申请人：LIU SHOW-WEN

  公开号：US20120009669A1

  公开（公告）日：2012-01-12

  A bifunctional compound with a monosaccharide and a N 2 S 2 ligand, and more particularly, a bifunctional compound with a N 2 S 2 ligand and aminohexylacetyl galactosamine (ah-GalNAc 4 ) is provided. A method for preparing the bifunctional compound with a monosaccharide and a N 2 S 2 ligand is also provided, including activating a carboxyl group in an organic ligand, reacting the activated carboxyl group with a galactopyranoside through amidation, and then hydrolyzing. The bifunctional compound of the present invention is widely useful in nuclear medicine for preparation of liver imaging agents for assisting in correct diagnosis of diseases.

  提供了一种具有单糖和N2S2配体的双功能化合物，更具体地说，提供了一种具有N2S2配体和氨基己酰半乳糖胺（ah-GalNAc4）的双功能化合物。还提供了一种制备具有单糖和N2S2配体的双功能化合物的方法，包括激活有机配体中的羧基，通过酰胺化将激活的羧基与半乳糖苷反应，然后水解。本发明的双功能化合物在核医学中广泛用于制备肝脏成像剂，以帮助正确诊断疾病。
• AURONE DERIVATIVE-CONTAINING COMPOSITION FOR DIAGNOSIS
  申请人：Nagasaki University

  公开号：EP2113258A1

  公开（公告）日：2009-11-04

  The present invention provides a composition for diagnosing amyloid-related diseases, comprising a compound represented by general formula (I): wherein X represents O or the like; R1, R3, R4, R5, R6, R8 and R9 represent a hydrogen atom or the like; R2 represents a halogen atom or the like; and R7 represents a dimethylamino group or the like; or the compound labeled with a radionuclide, or a pharmaceutically acceptable salt of the compound or the labeled compound. The compound represented by general formula (I) has all of the following properties: high binding specificity to amyloid β protein, high permeability through the blood-brain barrier, and rapid clearance from sites without senile plaques in the brain.

  本发明提供了一种用于诊断淀粉样蛋白相关疾病的组合物，包括由通式（I）表示的化合物： 其中X代表O或类似物；R1、R3、R4、R5、R6、R8和R9代表氢原子或类似物；R2代表卤原子或类似物；R7代表二甲氨基基团或类似物； 或者标记有放射性核素的化合物，或者化合物或标记化合物的药用盐。通式（I）表示的化合物具有以下所有特性：对淀粉样β蛋白具有高结合特异性，能够高透过血脑屏障，以及在大脑中无老年斑块的部位迅速清除。
• COMPOSITION FOR DIAGNOSING AMYLOID-RELATED DISEASE
  申请人：Nagasaki University

  公开号：EP2030635A1

  公开（公告）日：2009-03-04

  There is provided a composition comprising a compound represented by general formula (I), wherein R1 represents a 5-iodothiophen-2-yl group or the like, and R2 represents a 4-dimethylaminophenyl group or the like. This composition is useful for diagnosis of an amyloid-related disease such as Alzheimer's disease because the compound has high binding specificity to amyloid β protein, high permeability through the blood-brain barrier, and a property of being rapidly eliminated from sites other than senile plaques in the brain.

  提供了一种化合物组合物，其由一般式（I）表示的化合物组成，其中R1代表5-碘噻吩-2-基基团或类似物，R2代表4-二甲氨基苯基团或类似物。该组合物对于诊断与淀粉样蛋白相关的疾病，如阿尔茨海默病，具有高结合特异性，高透过血脑屏障的渗透性，以及在大脑老年斑以外部位迅速被排除的特性。
• Bisamidate and Mixed Amine/Amidate NiN₂S₂ Complexes as Models for Nickel-Containing Acetyl Coenzyme A Synthase and Superoxide Dismutase: An Experimental and Computational Study
  作者：Vaidyanathan Mathrubootham、Jason Thomas、Richard Staples、John McCraken、Jason Shearer、Eric L. Hegg

  DOI：10.1021/ic9023053

  日期：2010.6.21

  The distal nickel site of acetyl-CoA synthase (Nid-ACS) and reduced nickel superoxide dismutase (Ni-SOD) display similar square-planar NiIIN2S2 coordination environments. One difference between these two sites, however, is that the nickel ion in Ni-SOD contains a mixed amine/amidate coordination motif while the Nid site in Ni-ACS contains a bisamidate coordination motif. To provide insight into the

  乙酰辅酶A合酶（Ni d -ACS）和还原镍超氧化物歧化酶（Ni-SOD）的远端镍位点显示出类似的方形平面Ni II N 2 S 2配位环境。然而，这两个位点之间的一个区别是 Ni-SOD 中的镍离子包含混合的胺/酰胺配位基序，而Ni-ACS 中的 Ni d位点包含双酰胺基配位基序。为了深入了解不同配位环境对 Ni 离子性质的影响，我们系统地检查了两种方形平面 Ni II N 2 S 2复合物，一种具有双硫醇-双酰胺连接 (Et 4 N)2 (Ni(L1))·2H 2 O ( 2 ) [H 4 L1 = N -(2-巯基乙酰基)- N '-(2-巯基乙基)甘氨酰胺] 和另一个与双硫醇胺/酰胺基连接 K(Ni( HL2)) ( 3 ) [H 4 L2 = N -(2''-巯基乙基)-2-((2'-巯基乙基)氨基)乙酰胺]。尽管这两种配合物的区别仅在于单个胺与酰胺配体，但它们的化学性质却大不相同。双酰胺配合物
• COMPOUND HAVING AFFINITY WITH CALCIFIED TISSUE
  申请人：NIHON MEDI-PHYSICS CO., LTD.

  公开号：EP1609797A1

  公开（公告）日：2005-12-28

  The present invention provides a compound excellent in accumulation on calcified tissues and ensuring rapid excretion into urine as well as rapid clearance from blood, useful as a diagnostic agent and a therapeutic agent, etc. The compound is a compound having affinity with a calcified tissue represented by the following formula: (AC)a-MC-(LI)b. In the formula, MC is a mother nucleus and represents a residue of a compound having a plurality of functional groups selected from the group consisting of an amino group, an amide group, a hydroxyl group, a thiol group, a thioether group, a sulfonyl group a phosphonyl group, an aldehyde group, a carboxyl group, a carbonyl group, a halogen, and a cyano group; AC is a group having affinity with a calcified tissue; LI is a ligand for binding to a metal atom; and a is an integer of 1 or more and b is 0 or an integer of 1 or more.

  本发明提供了一种在钙化组织上具有出色积累并确保快速从尿液中排出以及从血液中迅速清除的化合物，可用作诊断剂和治疗剂等。该化合物是与以下公式表示的钙化组织具有亲和力的化合物：(AC)a-MC-(LI)b。在该公式中，MC是母核，表示由多个功能基团中的一种或多种选择组成的残基化合物，该多个功能基团包括氨基、酰胺基、羟基、硫醇基、硫醚基、磺酰基、膦酸基、醛基、羧基、酰基、卤素和氰基；AC是具有钙化组织亲和力的基团；LI是与金属原子结合的配体；a是1或更多的整数，b是0或1或更多的整数。